CN106458853A - 一种不对称还原法制备西他列汀中间体的方法 - Google Patents

一种不对称还原法制备西他列汀中间体的方法 Download PDF

Info

Publication number
CN106458853A
CN106458853A CN201580024946.4A CN201580024946A CN106458853A CN 106458853 A CN106458853 A CN 106458853A CN 201580024946 A CN201580024946 A CN 201580024946A CN 106458853 A CN106458853 A CN 106458853A
Authority
CN
China
Prior art keywords
acid
compound
hydrogen
ammonium
ammonium salt
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
Application number
CN201580024946.4A
Other languages
English (en)
Other versions
CN106458853B (zh
Inventor
洪健
王育盛
汪博宇
黄鲁宁
顾虹
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Zhejiang Huahai Pharmaceutical Co Ltd
Original Assignee
Zhejiang Huahai Pharmaceutical Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Zhejiang Huahai Pharmaceutical Co Ltd filed Critical Zhejiang Huahai Pharmaceutical Co Ltd
Publication of CN106458853A publication Critical patent/CN106458853A/zh
Application granted granted Critical
Publication of CN106458853B publication Critical patent/CN106458853B/zh
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • C07C29/15—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 oxides of carbon exclusively
    • C07C29/151—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 oxides of carbon exclusively with hydrogen or hydrogen-containing gases
    • C07C29/153—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 oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/14—Phosphorus; Compounds thereof
    • B01J27/16—Phosphorus; Compounds thereof containing oxygen, i.e. acids, anhydrides and their derivates with N, S, B or halogens without carriers or on carriers based on C, Si, Al or Zr; also salts of Si, Al and Zr
    • B01J27/18—Phosphorus; Compounds thereof containing oxygen, i.e. acids, anhydrides and their derivates with N, S, B or halogens without carriers or on carriers based on C, Si, Al or Zr; also salts of Si, Al and Zr with metals other than Al or Zr
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/30—Preparation of optical isomers
    • C07C227/32—Preparation of optical isomers by stereospecific synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
    • C07C25/02—Monocyclic aromatic halogenated hydrocarbons
    • C07C25/13—Monocyclic aromatic halogenated hydrocarbons containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C269/04—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • 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
    • C07C29/15—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 oxides of carbon exclusively
    • C07C29/151—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 oxides of carbon exclusively with hydrogen or hydrogen-containing gases
    • C07C29/1512—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 oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by reaction conditions
    • C07C29/1514—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 oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by reaction conditions the solvents being characteristic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/44—Allylic alkylation, amination, alkoxylation or analogues
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/001—General concepts, e.g. reviews, relating to catalyst systems and methods of making them, the concept being defined by a common material or method/theory
    • B01J2531/002—Materials
    • B01J2531/004—Ligands

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

本发明涉及一种合成西他列汀中间体的方法。该方法包括将式II化合物与氨或铵盐在手性膦配位的过渡金属催化剂以及氢气存在下，在加入酸性添加剂的条件下，在合适的有机溶剂中不对称还原氨化反应以得到式I化合物，其中立构中心的R‑或S‑构型用*表示，R构型的式I化合物可用于制备西他列汀，反应式如下：其中R1和R2各自独立地选自氢、C1‑C12直链或支链烷基、C3‑C12环烷基、C2‑C12链烯基、C2‑C12链炔基、C7‑C12芳基烷基。该方法的收率及ee％值高、反应条件温和、操作简单、便于纯化、生产成本低廉、对环境友好、适合工业化生产。

Description

PCT国内申请，说明书已公开。

Claims (11)

  1. PCT国内申请，权利要求书已公开。
CN201580024946.4A 2014-10-11 2015-10-09 一种不对称还原法制备西他列汀中间体的方法 Active CN106458853B (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CN201410532331.XA CN105566138A (zh) 2014-10-11 2014-10-11 一种合成西他列汀中间体的方法
CN201410532331X 2014-10-11
PCT/CN2015/091539 WO2016055015A1 (zh) 2014-10-11 2015-10-09 一种不对称还原法制备西他列汀中间体的方法

Publications (2)

Publication Number Publication Date
CN106458853A true CN106458853A (zh) 2017-02-22
CN106458853B CN106458853B (zh) 2020-03-27

Family

ID=55652600

Family Applications (2)

Application Number Title Priority Date Filing Date
CN201410532331.XA Pending CN105566138A (zh) 2014-10-11 2014-10-11 一种合成西他列汀中间体的方法
CN201580024946.4A Active CN106458853B (zh) 2014-10-11 2015-10-09 一种不对称还原法制备西他列汀中间体的方法

Family Applications Before (1)

Application Number Title Priority Date Filing Date
CN201410532331.XA Pending CN105566138A (zh) 2014-10-11 2014-10-11 一种合成西他列汀中间体的方法

Country Status (5)

Country Link
US (1) US10189760B2 (zh)
EP (1) EP3156391B1 (zh)
CN (2) CN105566138A (zh)
ES (1) ES2817909T3 (zh)
WO (1) WO2016055015A1 (zh)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106892832B (zh) * 2017-03-14 2019-06-25 珠海联邦制药股份有限公司 一种西格列汀杂质及其制备方法
CN111057061A (zh) * 2019-12-25 2020-04-24 台州保灵药业有限公司 一种叔丁氧羰基-西他列汀的制备方法
US11110444B2 (en) 2019-12-30 2021-09-07 Industrial Technology Research Institute Chiral catalyst and heterogeneous chiral catalyst comprising the same
CN115894310A (zh) * 2021-08-13 2023-04-04 江苏正大清江制药有限公司 阿普斯特手性胺中间体新的制备方法
CN114349648A (zh) * 2021-12-14 2022-04-15 深圳先进技术研究院 一种手性胺类化合物的制备方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005028419A2 (en) * 2003-09-18 2005-03-31 Takasago International Corporation Asymmetric reductive amination of keto acid derivatives for producing amino acid derivatives
WO2009064476A1 (en) * 2007-11-13 2009-05-22 Teva Pharmaceutical Industries Ltd. Preparation of sitagliptin intermediate
CN102702205A (zh) * 2012-05-16 2012-10-03 苏州新凯生物医药技术有限公司 西他列汀的制备方法
CN103755596A (zh) * 2013-09-30 2014-04-30 浙江工业大学 一种西他列汀中间体的制备方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005028419A2 (en) * 2003-09-18 2005-03-31 Takasago International Corporation Asymmetric reductive amination of keto acid derivatives for producing amino acid derivatives
WO2009064476A1 (en) * 2007-11-13 2009-05-22 Teva Pharmaceutical Industries Ltd. Preparation of sitagliptin intermediate
CN102702205A (zh) * 2012-05-16 2012-10-03 苏州新凯生物医药技术有限公司 西他列汀的制备方法
CN103755596A (zh) * 2013-09-30 2014-04-30 浙江工业大学 一种西他列汀中间体的制备方法

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
DIETRICH STEINHUEBEL等: "Direct Asymmetric Reductive Amination", 《J. AM. CHEM. SOC.》 *
JIAN-HUA XIE: "Recent advances in transition metal-catalyzed enantioselective hydrogenation of unprotected enamines", 《CHEM. SOC. REV.》 *
KAZUHIKO MATSUMURA等: "Practical, Catalytic Enantioselective Hydrogenation to Synthesize N-Unprotected β-Amino Esters", 《ORG. PROCESS RES. DEV.》 *

Also Published As

Publication number Publication date
US10189760B2 (en) 2019-01-29
ES2817909T3 (es) 2021-04-08
EP3156391A4 (en) 2018-01-17
US20170305822A1 (en) 2017-10-26
EP3156391B1 (en) 2020-09-02
CN106458853B (zh) 2020-03-27
EP3156391A1 (en) 2017-04-19
WO2016055015A1 (zh) 2016-04-14
CN105566138A (zh) 2016-05-11

Similar Documents

Publication Publication Date Title
CN106458853A (zh) 一种不对称还原法制备西他列汀中间体的方法
CN115073312B (zh) 一种重酒石酸去甲肾上腺素合成方法
Tang et al. Synthesis of a water-soluble cationic chiral diamine ligand bearing a diguanidinium and application in asymmetric transfer hydrogenation
US8471016B2 (en) Process for the preparation of chiral beta amino carboxamide derivatives
CN106674084B (zh) 一种2-异丙基氧基-5-甲基-4-(哌啶-4-基)苯胺二盐酸盐的制备方法
CN111233673B (zh) 一种手性芳香族环丙胺及其盐的制备方法及所用中间体
CN101781222A (zh) 一种制备烯胺酮类化合物的方法
CN104326927B (zh) 一种1-[2-氨基-1-(4-甲氧基苯基)乙基]环己醇硫酸盐的制备方法
CN113754605B (zh) 一种含氮配体及其制备方法和应用
CN103922943B (zh) 一种制备盐酸芬戈莫德的方法
CN109574938B (zh) 一种瑞舒伐他汀钠的合成方法
CN107827916B (zh) 一种(r)-(1-氨基-3-甲基)丁基-1-硼酸蒎烷二醇酯的合成方法
CN109836374B (zh) 一种维生素b6的环保制备方法
CN111574458A (zh) 一种麦角硫因的合成方法
CN106008363B (zh) 2-甲基-4-氨基-5-氰基嘧啶的制备方法
CN110627672B (zh) 一种磷酸二甲啡烷及其中间体的制备方法
CN113620869B (zh) 一种贝曲西班的制备方法
CN102964256B (zh) 一种4-氨基-n,n-二甲基苄胺的制备方法
CN107445879B (zh) 拉曲替尼中间体的制备方法
CN109776400B (zh) 一种(r)-苯基(吡啶-2-基)甲醇衍生物的制备方法
CN109665967B (zh) 茚类化合物不对称环氧化反应用配体及其制备方法与应用
CN101863821B (zh) 一种以手性脯氨酸酯为原料制备手性肼的方法
CN109836373B (zh) 一种维生素b6的环保制备及尾气循环利用的方法
CN111362824B (zh) 2-(氨甲基)-n,n-二乙基-1-苯基环丙烷甲酰胺及其盐的制备方法
CN101506146B (zh) 3-氨基-5-氟-4-二烷氧基戊酸酯的制备方法

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant