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1. 发明授权

US5859249A 2-phenyl-2-(2'-piperidinylidene)acetate derivative, process for manufacturing the same, and process for manufacturing optically active 2-phenyl-2-(2'-piperidinyl)acetate derivative by asymmetrically hydrogenating the same 失效
标题翻译： 2-苯基-2-（2'-亚哌啶基）乙酸酯衍生物，其制备方法，以及通过不对称氢化其制备光学活性2-苯基-2-（2'-哌啶基）乙酸酯衍生物的方法
公开(公告)号：US5859249A
公开(公告)日：1999-01-12
申请号：US895428
申请日：1997-07-16
申请人： Nobuo Seido , Takenobu Nishikawa , Tsukasa Sotoguchi , Yoshifumi Yuasa , Takashi Miura , Hidenori Kumobayashi
发明人： Nobuo Seido , Takenobu Nishikawa , Tsukasa Sotoguchi , Yoshifumi Yuasa , Takashi Miura , Hidenori Kumobayashi
IPC分类号： C07C229/34 , C07C271/22 , C07D211/70 , C07D211/02 , C07D211/32
CPC分类号： C07C229/34 , C07C271/22 , C07D211/70
摘要： Disclosed is a 2-phenyl-2-(2'-piperidinylidene)acetate derivative suitably used for a raw material of a 2-phenyl-2-(2'-piperidinyl)acetate derivative and a process for manufacturing the same. Also disclosed is a process for manufacturing an optically active 2-phenyl-2-(2'-piperidinyl)acetate derivative which is a major intermediate for an antidepressant. The 2-phenyl-2-(2'-piperidinylidene)acetate derivative is manufactured by cyclizing a 7-(N-substituted amino)-3-oxo-2-heptanoate derivative. The optically active 2-phenyl-2-(2'-piperidinyl)acetate derivative is manufactured by asymmetrically hydrogenating the 2-phenyl-2-(2'-piperidinylidene)acetate derivative in the presence of a complex of a Group VIII transition metal or an acid.
摘要翻译：公开了适用于2-苯基-2-（2'-哌啶基）乙酸酯衍生物的原料的2-苯基-2-（2'-亚哌啶基）乙酸酯衍生物及其制造方法。还公开了作为抗抑郁药的主要中间体的光学活性2-苯基-2-（2'-哌啶基）乙酸酯衍生物的制造方法。通过使7-（N-取代的氨基）-3-氧代-2-庚酸酯衍生物环化制备2-苯基-2-（2'-亚哌啶基）乙酸酯衍生物。光学活性的2-苯基-2-（2'-哌啶基）乙酸酯衍生物是通过在第VIII族过渡金属络合物存在下不对称氢化2-苯基-2-（2'-亚哌啶基）乙酸酯衍生物制备的，酸。

2. 发明授权

US5942629A Process for producing optically active pyrrolidine derivatives 失效
标题翻译：光学活性吡咯烷衍生物的制备方法
公开(公告)号：US5942629A
公开(公告)日：1999-08-24
申请号：US976491
申请日：1997-11-24
申请人： Yoshifumi Yuasa , Tsukasa Sotoguchi , Nobuo Seido
发明人： Yoshifumi Yuasa , Tsukasa Sotoguchi , Nobuo Seido
IPC分类号： B01J31/24 , C07B61/00 , C07D207/08 , C07D207/09 , C07D207/26
CPC分类号： C07D207/08 , C07D207/09 , C07D207/26
摘要： A production process for obtaining optically active (3R,1'S)-1-benzyl-3-�(1'-N-methylamino)ethyl!pyrrolidine or (3R,1'S)-3-�(1'-N-methylamino)ethyl!pyrrolidine used as an intermediate for the synthesis of pharmaceutical preparations such as anti-fungal agents in high purity and in high yield using a reduced number of processing steps. The process comprises asymmetrically hydrogenating 3-acetyl-1-benzyl-2-pyrrolidinone in the presence of a complex formed from bidentate phosphine and ruthenium as a catalyst to provide (3S,1'R)-1-benzyl-3-�(1'-hydroxy)ethyl!-2-pyrrolidinone, then reducing with a hydride to provide (3R,1'R)-1-benzyl-3-�(1'-hydroxy)ethyl!pyrrolidine, mesylating or tosylating to provide (3R,1'R)-1-benzyl-3-�(1'-methanesulfonyloxy)ethyl!pyrrolidine or (3R,1'R)-1-benzyl-3-�(1'-p-toluenesulfonyloxy)ethyl!pyrrolidine, and reacting with methylamine to obtain (3R,1'S)-1-benzyl-3-�(1'-N-methylamino)ethyl!pyrrolidine. The prcess may further comprise de-benzylating (3R,1'S)-1-benzyl-3-�(1'-N-methylamino)ethyl!pyrrolidine to obtain (3R,1'S)-3-�(1'-N-methylamino)ethyl!pyrrolidine.
摘要翻译：制备光学活性（3R，1'S）-1-苄基-3 - [（1'-N-甲基氨基）乙基]吡咯烷或（3R，1'S）-3 - [（1'-N-甲基氨基）乙基 ]吡咯烷，其用作用于合成药物制剂例如抗真菌剂的中间体，其使用减少数量的加工步骤以高纯度和高产率。该方法包括在二齿膦和钌作为催化剂形成的络合物存在下不对称氢化3-乙酰基-1-苄基-2-吡咯烷酮，得到（3S，1'R）-1-苄基-3 - [（1 然后用氢化物还原得到（3R，1'R）-1-苄基-3 - [（1'-羟基）乙基]吡咯烷，甲磺酰化或甲苯磺酸化，得到（3R ，1'R）-1-苄基-3 - [（1'-甲磺酰氧基）乙基]吡咯烷或（3R，1'R）-1-苄基-3 - [（1'-对甲苯磺酰氧基）乙基] 并与甲胺反应，得到（3R，1'S）-1-苄基-3 - [（1'-N-甲基氨基）乙基]吡咯烷。进一步包括脱苄基化（3R，1'S）-1-苄基-3 - [（1'-N-甲基氨基）乙基]吡咯烷，得到（3R，1'S）-3 - [（1'-N-甲基氨基）乙基]吡咯烷。

3. 发明授权

US5801271A 7-(n-substituted amino)-2-phenylheptanoic acid derivative and process for manufacturing the same 失效
标题翻译： 7-（正取代氨基）-2-苯基庚酸衍生物及其制造方法
公开(公告)号：US5801271A
公开(公告)日：1998-09-01
申请号：US895429
申请日：1997-07-16
申请人： Nobuo Seido , Takenobu Nishikawa , Tsukasa Sotoguchi , Yoshifumi Yuasa , Takashi Miura , Hidenori Kumobayashi
发明人： Nobuo Seido , Takenobu Nishikawa , Tsukasa Sotoguchi , Yoshifumi Yuasa , Takashi Miura , Hidenori Kumobayashi
IPC分类号： B01J31/02 , B01J31/22 , C07B61/00 , C07C229/34 , C07C269/06 , C07C271/18 , C07C271/22 , C07C303/28 , C07C309/73 , C07C271/06
CPC分类号： C07C271/22 , C07C229/34 , Y02P20/55
摘要： Disclosed is a 7-(N-substituted amino)-3-oxo-2-phenylheptanoate derivative, 7-(N-substituted amino)-3-hydroxy-2-phenylheptanoate derivative, and 7-(N-substituted amino)-3-benzenesulfonyloxy-2-phenylheptanoate derivative, which are quite important major intermediates for an antidepressant. The 7-(N-substituted amino)-3-oxo-2-phenylheptanoate derivative can be manufactured by condensing an enolate of phenylacetates with a 5-(N-substituted amino) pentanoate derivative.
摘要翻译：公开了7-（N-取代氨基）-3-氧代-2-苯基庚酸酯衍生物，7-（N-取代氨基）-3-羟基-2-苯基庚酸酯衍生物和7-（N-取代氨基）-3 - 苯磺酰氧基-2-苯基庚酸酯衍生物，它们是抗抑郁药的重要主要中间体。 7-（N-取代氨基）-3-氧代-2-苯基庚酸酯衍生物可以通过将苯乙酸酯的烯醇化物与5-（N-取代的氨基）戊酸酯衍生物缩合来制备。

4. 发明授权

US6008358A Process for the preparation of piperidinylidene derivative 失效
标题翻译：制备亚哌啶基衍生物的方法
公开(公告)号：US6008358A
公开(公告)日：1999-12-28
申请号：US69114
申请日：1998-04-29
申请人： Takenobu Nishikawa , Nobuo Seido
发明人： Takenobu Nishikawa , Nobuo Seido
IPC分类号： B01J31/22 , C07B61/00 , C07D211/70 , C07D211/34 , C07D211/60 , C07D211/76
CPC分类号： C07D211/70
摘要： Disclosed is a process for economic, safe and simple production of a 2-phenyl-2-(2'-piperidinylidene)acetate derivative at a reduced number of steps in a high yield, which comprises allowing 2,3,4,5-Tetrahydro-6-methoxypyridine and a benzyl cyanide derivative represented by the following general formula (2): wherein R.sup.1 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or an amino group, to undergo condensation reaction in the presence of an organic base such as 1,8-diazabicyclo[5.4.0]-7-undecene or a transition metal complex as a catalyst to produce a 2-phenyl-2-(2'-piperidinylidene)acetonitrile derivative represented by the following general formula (4): ##STR1## wherein R.sup.1 is as defined above; and the wavy line indicates a geometrical isomer, and then reacting with an alcohol in the presence of hydrogen chloride.
摘要翻译：公开了以高产率以减少数量的步骤经济，安全和简单地生产2-苯基-2-（2'-亚哌啶基）乙酸酯衍生物的方法，其包括使2,3,4,5-四氢 -6-甲氧基吡啶和由以下通式（2）表示的苄基氰化物衍生物：其中R1表示氢原子，低级烷基，低级烷氧基，卤素原子或氨基，在存在有机碱如1,8-二氮杂双环[5.4.0] -7-十一碳烯或过渡金属络合物作为催化剂，以制备由以下化合物表示的2-苯基-2-（2'-亚哌啶基）乙腈衍生物通式（4）：其中R1如上所定义; 并且波浪线表示几何异构体，然后在氯化氢存在下与醇反应。

5. 发明授权

US5763688A Method for producing an alcohol 失效
标题翻译：醇的制造方法
公开(公告)号：US5763688A
公开(公告)日：1998-06-09
申请号：US568589
申请日：1995-12-07
申请人： Takao Ikariya , Takeshi Ohkuma , Hirohito Ooka , Shohei Hashiguchi , Nobuo Seido , Ryoji Noyori
发明人： Takao Ikariya , Takeshi Ohkuma , Hirohito Ooka , Shohei Hashiguchi , Nobuo Seido , Ryoji Noyori
IPC分类号： C07B41/02 , C07B53/00 , C07C29/145 , C07C41/26 , C07C67/31 , C07D213/30 , C07F17/02 , C07C29/36
CPC分类号： C07D213/30 , C07B41/02 , C07B53/00 , C07C29/145 , C07C403/08 , C07C41/26 , C07C67/31 , C07F17/02 , C07B2200/07 , C07B2200/09 , C07C2101/14 , C07C2101/16 , C07C2102/10 , C07C2103/18 , C07C2103/26
摘要： The present invention provides a method for producing a alcohol including an optically active alcohol by hydrogenating a carbonyl compound in the presence of a homogeneous catalyst, a base and a nitrogen-containing organic compound. Thus, the reaction employs an inexpensive catalyst and proceeds in high yield and high efficiency.
摘要翻译：本发明提供通过在均相催化剂，碱和含氮有机化合物的存在下氢化羰基化合物来制备包含光学活性醇的醇的方法。因此，反应采用廉价的催化剂，并以高产率和高效率进行。

6. 发明授权

US5856590A Process for producing cis-4-t-butylcyclohexanol 失效
标题翻译：顺式-4-叔丁基环己醇的制备方法
公开(公告)号：US5856590A
公开(公告)日：1999-01-05
申请号：US812540
申请日：1997-03-07
申请人： Makoto Emura , Takaaki Toyoda , Nobuo Seido , Ryoji Noyori , Takao Ikariya , Takeshi Ohkuma
发明人： Makoto Emura , Takaaki Toyoda , Nobuo Seido , Ryoji Noyori , Takao Ikariya , Takeshi Ohkuma
IPC分类号： B01J31/24 , C07B61/00 , C07C29/145 , C07C35/08
CPC分类号： C07C29/145 , C07B2200/09 , C07C2101/14
摘要： A process whereby 4-t-butylcyclohexanol with a high content of the cis-isomer, which is useful as a perfume ingredient, can be economically produced on an industrially available scale at a low cost. The process comprises hydrogenating 4-t-butylcyclohexanone by using a specific ruthenium-phosphine complex as a catalyst in the presence of a base containing an alkali metal and an alkylenediamine having from 1 to 6 carbon atoms.
摘要翻译：可以以低成本在工业上可用的规模上经济地生产具有高含量的顺式异构体作为香料成分的4-叔丁基环己醇的方法。该方法包括在含有碱金属和具有1至6个碳原子的亚烷基二胺存在下使用特定的钌 - 膦配合物作为催化剂来氢化4-叔丁基环己酮。

7. 发明授权

US5750804A Process for producing trans-3-isocamphylcyclohexanol 失效
标题翻译：反式-3-异柠檬酰环己醇的制备方法
公开(公告)号：US5750804A
公开(公告)日：1998-05-12
申请号：US813238
申请日：1997-03-07
申请人： Makoto Emura , Takaaki Toyoda , Nobuo Seido , Makoto Harada , Ryoji Noyori , Takao Ikariya , Takashi Ohkuma
发明人： Makoto Emura , Takaaki Toyoda , Nobuo Seido , Makoto Harada , Ryoji Noyori , Takao Ikariya , Takashi Ohkuma
IPC分类号： B01J31/24 , C07B61/00 , C07C29/145 , C07C35/21 , C07C35/08
CPC分类号： C07C29/145 , C07B2200/09 , C07C2101/14 , C07C2102/42
摘要： A process whereby trans-3-isocamphylcyclohexanol, which is useful as a perfume ingredient, can be produced on an industrially available scale, at a low cost and at a high stereoselectivity, is disclosed. The process comprises hydrogenating 3-isocamphylcyclohexanone represented by the following formula (I): ##STR1## by using a ruthenium/phosphine complex as a catalyst in the presence of a base containing an alkali metal or an alkaline earth metal and an amine.
摘要翻译：可以以低成本和高立体选择性在工业上可用的规模生产可用作香料成分的反式-3-异柠檬酰环己醇的方法。该方法包括在含有碱金属或碱土金属和胺的碱的存在下，通过使用钌/膦配合物作为催化剂氢化由下式（I）表示的3-异冬酰胺环己酮：。

8. 发明授权

US5144042A Process for preparing optically active 3-hydroxypyrrolidine derivatives 失效
标题翻译：制备光学活性3-羟基吡咯烷衍生物的方法
公开(公告)号：US5144042A
公开(公告)日：1992-09-01
申请号：US682273
申请日：1991-04-09
申请人： Nobuo Seido , Yoshiki Okeda , Hidenori Kumobayashi
发明人： Nobuo Seido , Yoshiki Okeda , Hidenori Kumobayashi
IPC分类号： C07B53/00 , C07C31/34 , C07C211/27 , C07C309/65 , C07C309/73 , C07D207/12
CPC分类号： C07D207/12
摘要： A process for preparing optically active 3-hydroxypyrrolidine derivatives useful as intermediates represented by formula (III): ##STR1## wherein Q represents a substituted or unsubstituted phenyl group; and * indicates an asymmetric carbon atom, comprising reacting an optically active 4-halo-3-hydroxybutane derivative represented by formula (I): ##STR2## wherein * is as defined above; R.sup.1 represents a lower alkyl group or a substituted or unsubstituted phenyl group; and X represents a halogen atom, with a benzylamine derivative represented by formula (II):H.sub.2 NCH.sub.2 Q (II)wherein Q is as defined above, is disclosed. The starting compound (I) is easily available through chemical synthesis. Any complicated procedure or use of an expensive reagent is not required.

9. 发明授权

US5081310A Process for preparing optically active ketones 失效
标题翻译：制备光学活性酮的方法
公开(公告)号：US5081310A
公开(公告)日：1992-01-14
申请号：US553285
申请日：1990-07-17
申请人： Nobuo Seido , Hidenori Kumobayashi
发明人： Nobuo Seido , Hidenori Kumobayashi
IPC分类号： B01J31/24 , C07B61/00 , C07C45/62 , C07C49/395 , C07C49/403
CPC分类号： C07C49/395 , C07C45/62 , C07C49/403
摘要： A process for preparing an optically active ketone represented by formula (I): ##STR1## wherein R.sup.1 represents a hydrogen atom or an alkyl group having from 1 to 5 carbon atoms; and n represents 1 or 2,which comprises asymmetrically hydrogenating an .alpha., .beta.-unsaturated ketone represented by formula (II): ##STR2## wherein R.sup.1 and n are as defined above, in the presence of a ruthenium-optically active phosphine complex as a catalyst. An optically active ketone having a high optical purity can be prepared.

10. 发明授权

US4994602A Process for preparing optically active 6-t-butyoxy-3,5-dihydroxyhexanoic esters 失效
标题翻译：光学活性6-叔丁氧基-3,5-二羟基己酸酯的制备方法
公开(公告)号：US4994602A
公开(公告)日：1991-02-19
申请号：US485692
申请日：1990-02-27
申请人： Nobuo Seido , Noboru Sayo , Hidenori Kumobayashi
发明人： Nobuo Seido , Noboru Sayo , Hidenori Kumobayashi
IPC分类号： C07C67/31 , C07C69/708
CPC分类号： C07C67/31 , C07C69/708
摘要： A process for preparing an optically active 6-t-butoxy-3,5-dihydroxyhexanoic ester represented by formula: ##STR1## wherein t-Bu represents a t-butyl group; and R.sup.4 represents a lower alkyl group, which is useful as a precursor of a lactone moiety of campactin, mevinolin or analogues thereof is disclosed, comprising asymmetrically hydrogenating a 4-t-butoxyacetoacetic ester in the presence of a ruthenium-optically active phosphine complex to obtain an optically active 4-t-butyoxy-3-hydroxybutanoic ester, reacting the ester with a lithium enolate of an acetic ester to obtain an optically active 6-t-butyoxy-5-hydroxy-3-oxohexanoic ester, and asymmetrically hydrogenating the resulting ester in the presence of a ruthenium-optically active phosphine complex as a catalyst. The desired product can be obtained in good yield at high stereoselectivity.

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