JPH10501530A - テトラヒドロインデノ〔1,2−d〕〔1,3,2〕オキサザボロール及びその鏡像異性体選択性触媒としての使用 - Google Patents
テトラヒドロインデノ〔1,2−d〕〔1,3,2〕オキサザボロール及びその鏡像異性体選択性触媒としての使用Info
- Publication number
- JPH10501530A JPH10501530A JP8501029A JP50102996A JPH10501530A JP H10501530 A JPH10501530 A JP H10501530A JP 8501029 A JP8501029 A JP 8501029A JP 50102996 A JP50102996 A JP 50102996A JP H10501530 A JPH10501530 A JP H10501530A
- Authority
- JP
- Japan
- Prior art keywords
- hydrogen
- phenyl
- alkyl
- aryl
- borane
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/20—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/02—Boron compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.R1が水素、アルキル、アリールメチレン、又はヘテロアリールメチレンで あり、 R2がアルキル、ベンジル、フェニル、又は置換フェニルであり、 R4が水素、アルキル、アリール、ハロ、ニトロ、又はアルコキシである、 で構成されるグループの中から選定した触媒作用のある量の化合物の存在の下に 、不活性溶媒中のボラン還元作用物質と前駆体キラル ケトンとを反応させるこ とを包含する、前駆体キラル ケトンの鏡像異性体特定還元方法。 2.前記ボラン還元作用物質が硫化ボラン−メチル又はボラン−THFである、 請求項1に記載した方法。 3.R2が水素、メチル、ブチル、又はフェニルであり、R4が水素である、請求 項1に記載した方法。 4.R1が水素であり、R2が水素、メチル、ブチル、又はフェニルである、請求 項1に記載した方法。 5.前記ケトンが、Arがアリール又は置換アリールであり、R5が水素又はハ ロゲンである、化学式 のものである、請求項1に記載した方法。 6.Arがフェニル、アルキルフェニル、クロルフェニル、オキシフェニル、ア ルコキシフェニル、ニトロフェニル、又はナフチルである、請求項5に記載した 方法。 7.(a)R3がアルキル、アリール、又はヘテロアリールであり、R4が水素、 アルキル、アリール、ハロ、又はアルコキシである、化学式 の化合物と、少なくとも1当量のボラン還元作用物質とを、触媒混合剤を提供す るために不活性溶媒の中で化合させることと、 (b)前記触媒混合剤に1当量以上の前駆体キラル ケトンと対応する量のボ ラン還元作用物質とを加えることと、 を包含する前駆体キラル ケトンの鏡像異性体選択性還元プロセス。 8.前記ボラン還元作用物質が硫化ボラン−メチル又はボラン−THFである、 請求項7に記載したプロセス。 9.R3がフェニル、フラン、又はピロールである、請求項7に記載したプロセ ス。 10.前記ケトンが、Arがアリール又は置換アリールであり、R5が水素又は ハロゲンである、化学式 のものである、請求項7に記載したプロセス。 11.Arがフェニル、アルキルフェニル、クロルフェニル、オキシフェニル、 アルコキシフェニル、ニトロフェニル、又はナフチルである、請求項10に記載 したプロセス。 12.R3がアルキル、アリール、又はヘテロアリールであり、R4が水素、アル キル、アリール、ハロ、ニトロ、又はアルコキシである、化学式が の化合物。 13.R3がフェニル、フラン、又はピロールであり、R4が水素である、請求項 12に記載した化合物。 14.R1が水素、アルキル、アリールメチレン、又はヘテロアリールメチレン であり、 R2がアルキル、ベンジル、フェニル、又は置換フェニルであり、 R4が水素、アルキル、アリール、ハロ、ニトロ、又はアルコキシであるが、 R1とR2とが共に水素ではあり得ないと云う条件を備える、 化学式が の化合物。 15.R2とR4とが共に水素である、請求項14に記載した化合物。 16.R1が水素であり、R2がメチル、ブチル、又はフェニルである、請求項1 4に記載した化合物。 17.R1がベンジル又はヘテロアリールメチレンである、請求項14に記載し た化合物。 18.R2とR4とが共に水素である、請求項17に記載した化合物。 19.R1aがヘテロアリールメチレンであり、 R4が水素、アルキル、アリール、ハロ、ニトロ、又はアルコキシである、 化学式が の化合物。 20.R1がピロリルメチル又はフラニルメチルである、請求項19に記載した 化合物。 21.R4が水素である、請求項19に記載した化合物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/250,821 | 1994-05-31 | ||
US08/250,821 US5495054A (en) | 1994-05-31 | 1994-05-31 | Tetrahydroindeno[1,2-D][1,3,2]oxazaboroles and their use as enantioselective catalysts |
PCT/US1995/006615 WO1995032937A1 (en) | 1994-05-31 | 1995-05-24 | TETRAHYDROINDENO[1,2-d][1,3,2]OXAZABOROLES AND THEIR USE AS ENANTIOSELECTIVE CATALYSTS |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH10501530A true JPH10501530A (ja) | 1998-02-10 |
JP3867250B2 JP3867250B2 (ja) | 2007-01-10 |
Family
ID=22949300
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP50102996A Expired - Lifetime JP3867250B2 (ja) | 1994-05-31 | 1995-05-24 | テトラヒドロインデノ〔1,2−d〕〔1,3,2〕オキサザボロール及びその鏡像異性体選択性触媒としての使用 |
Country Status (12)
Country | Link |
---|---|
US (1) | US5495054A (ja) |
EP (1) | EP0763005B1 (ja) |
JP (1) | JP3867250B2 (ja) |
AT (1) | ATE195711T1 (ja) |
AU (1) | AU689595B2 (ja) |
CA (1) | CA2191073C (ja) |
DE (1) | DE69518516T2 (ja) |
DK (1) | DK0763005T3 (ja) |
ES (1) | ES2149991T3 (ja) |
GR (1) | GR3034809T3 (ja) |
PT (1) | PT763005E (ja) |
WO (1) | WO1995032937A1 (ja) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE69512002T2 (de) * | 1994-10-28 | 2000-05-25 | Sumitomo Chemical Co | Verfahren zur Herstellung von optisch aktiven Carbinolen |
ES2167541T3 (es) * | 1995-02-03 | 2002-05-16 | Kaneka Corp | Procedimientos de produccion de alfa-halocetonas, de alfa-halohidrinas y de epoxidos. |
JPWO2002051781A1 (ja) * | 2000-12-25 | 2004-04-22 | 味の素株式会社 | 光学活性ハロヒドリン化合物の製造方法 |
PE20040950A1 (es) | 2003-02-14 | 2005-01-01 | Theravance Inc | DERIVADOS DE BIFENILO COMO AGONISTAS DE LOS RECEPTORES ADRENERGICOS ß2 Y COMO ANTAGONISTAS DE LOS RECEPTORES MUSCARINICOS |
AU2005227733A1 (en) * | 2004-04-02 | 2005-10-13 | Glaxo Group Limited | Chemical process and new crystalline form |
US7423146B2 (en) | 2005-11-09 | 2008-09-09 | Boehringer Ingelheim International Gmbh | Process for the manufacturing of pharmaceutically active 3,1-benzoxazine-2-ones |
PE20080610A1 (es) | 2006-08-22 | 2008-07-15 | Boehringer Ingelheim Int | Nuevos beta-agonistas enantiomericamente puros, procedimientos para su preparacion y uso como medicamentos |
EP2093219A1 (de) | 2008-02-22 | 2009-08-26 | Boehringer Ingelheim International Gmbh | Kristalline, enantiomerenreine Salzform eines Betamimetikums und dessen Verwendung als Arzneimittel |
CN101747211A (zh) * | 2009-07-03 | 2010-06-23 | 凯莱英生命科学技术(天津)有限公司 | 一种手性β-氨基醇衍生物的合成方法及其部分最终产物 |
WO2011132083A2 (en) | 2010-04-20 | 2011-10-27 | Actavis Group Ptc Ehf | Novel process for preparing phenylcyclopropylamine derivatives using novel intermediates |
CN110627673B (zh) * | 2018-06-22 | 2023-04-07 | 上海天慈中商药业有限公司 | 一种福莫特罗关键中间体的制备方法 |
CN109748788B (zh) * | 2019-01-17 | 2021-05-14 | 南方科技大学 | ɑ-羟基酸制备方法 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4943635A (en) * | 1987-08-27 | 1990-07-24 | President & Fellows Of Harvard College | Enantioselective reduction of ketones |
US5039802A (en) * | 1990-04-18 | 1991-08-13 | Merck & Co., Inc. | Arylation process for preparation of chiral catalysts for ketone reduction |
US5189177A (en) * | 1990-04-18 | 1993-02-23 | Merck & Co., Inc. | Chiral boron catalysts for reduction of ketones and process for their preparation |
US5264585A (en) * | 1990-04-18 | 1993-11-23 | Merck & Co., Inc. | Chiral catalysts for reduction of ketones and process for their preparation |
US5157129A (en) * | 1990-04-18 | 1992-10-20 | Merck & Co., Inc. | Enantiospecific synthesis of s-(+)-5,6-dihydro-4-(r-amino)-4h-thieno(2,3-b)thiopyran-2-sulfonamide-7,7-dioxide |
JP2525127B2 (ja) * | 1992-05-14 | 1996-08-14 | ファイザー・インコーポレーテッド | 鏡像体選択的オキサアザボロリジン |
TW416958B (en) * | 1993-05-14 | 2001-01-01 | Pfizer | Enantioselective oxazaborolidine catalysts |
-
1994
- 1994-05-31 US US08/250,821 patent/US5495054A/en not_active Expired - Lifetime
-
1995
- 1995-05-24 DK DK95921397T patent/DK0763005T3/da active
- 1995-05-24 DE DE69518516T patent/DE69518516T2/de not_active Expired - Lifetime
- 1995-05-24 CA CA002191073A patent/CA2191073C/en not_active Expired - Lifetime
- 1995-05-24 PT PT95921397T patent/PT763005E/pt unknown
- 1995-05-24 AU AU26487/95A patent/AU689595B2/en not_active Expired
- 1995-05-24 JP JP50102996A patent/JP3867250B2/ja not_active Expired - Lifetime
- 1995-05-24 WO PCT/US1995/006615 patent/WO1995032937A1/en active IP Right Grant
- 1995-05-24 ES ES95921397T patent/ES2149991T3/es not_active Expired - Lifetime
- 1995-05-24 AT AT95921397T patent/ATE195711T1/de active
- 1995-05-24 EP EP95921397A patent/EP0763005B1/en not_active Expired - Lifetime
-
2000
- 2000-11-10 GR GR20000402496T patent/GR3034809T3/el unknown
Also Published As
Publication number | Publication date |
---|---|
WO1995032937A1 (en) | 1995-12-07 |
US5495054A (en) | 1996-02-27 |
ATE195711T1 (de) | 2000-09-15 |
CA2191073A1 (en) | 1995-12-07 |
AU689595B2 (en) | 1998-04-02 |
DK0763005T3 (da) | 2000-12-27 |
EP0763005B1 (en) | 2000-08-23 |
PT763005E (pt) | 2001-01-31 |
ES2149991T3 (es) | 2000-11-16 |
EP0763005A1 (en) | 1997-03-19 |
GR3034809T3 (en) | 2001-02-28 |
EP0763005A4 (en) | 1997-10-22 |
DE69518516T2 (de) | 2001-04-19 |
DE69518516D1 (de) | 2000-09-28 |
JP3867250B2 (ja) | 2007-01-10 |
CA2191073C (en) | 2007-07-17 |
AU2648795A (en) | 1995-12-21 |
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