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Title:
METHOD FOR PREPARING 5R-BENZYLOXYAMINOPIPERIDIN-2S-CARBOXYLIC ACID OR DERIVATIVE THEREOF
Document Type and Number:
WIPO Patent Application WO/2019/127902
Kind Code:
A1
Abstract:
The present invention relates to a green method for preparing 5R-benzyloxyaminopiperidin-2S-carboxylic acid or derivatives thereof. According to the method, L-glutamic acid, used as a starting raw material, is subjected to esterification in the presence of an acidic reagent, and is then successively reacted with 2-haloacetate and an N-protective reagent, or the N-protective reagent and the 2-haloacetate under alkaline conditions to obtain a compound IV, wherein same is then subjected to ring formation by intramolecular condensation under the action of strong base to obtain an N-protective group piperidin-5-one-2S-carboxylate (V). The resulting compound V is sujected to one of the following routes for preparing the 5R-benzyloxyaminopiperidin-2S-carboxylic acid (or carboxylate): route 1: the compound V is subjected to protective group-removing, condensation with a benzyloxy ammonia hydrochloride, imine-reduction-chiral resolution, neutralization, and hydrolysis; route 2: hydrolysis of the compound V, protective group removing, condensation of benzyloxy ammonia hydrochloride, reduction-chiral resolution of imine, and neutralization; and route 3: the compound V is subjected to condensation with benzyloxy ammonia hydrochloride, imine-reduction-chiral resolution, protective group-removing, neutralization, and hydrolysis. This route can be achieved by a "one pot method".

Inventors:
QI YUXIN (CN)
LI XINFA (CN)
XU XIN (CN)
WANG BAOLIN (CN)
QU HU (CN)
XIE SHUNGEN (CN)
Application Number:
CN2018/078072
Publication Date:
July 04, 2019
Filing Date:
March 06, 2018
Export Citation:
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Assignee:
XINFA PHARMACEUTICAL CO LTD (CN)
International Classes:
C07D211/02; C07B57/00; C07D211/60; C07D211/68
Domestic Patent References:
WO2010126820A22010-11-04
WO2012172368A12012-12-20
Foreign References:
CN107540601A2018-01-05
US20100197928A12010-08-05
US20130012712A12013-01-10
US20140275001A12014-09-18
Attorney, Agent or Firm:
JINAN JINDI INTELLECTUAL PROPERTY AGENCY CO., LTD. (CN)
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