An efficient stereoselective synthesis of methyl (S)-3-amino-3-(3-pyridyl)propanoate

Authors
Zhong, HM Cohen, JH Abdel-Magid, AF Kenney, BD Maryanoff, CA Shah, RD Villani, FJ Zhang, F Zhang, XN
Citation
Hm. Zhong et al., An efficient stereoselective synthesis of methyl (S)-3-amino-3-(3-pyridyl)propanoate, TETRAHEDR L, 40(44), 1999, pp. 7721-7725
Citations number
17
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
44
Year of publication
1999
Pages
7721 - 7725
Database
ISI
SICI code
0040-4039(19991029)40:44<7721:AESSOM>2.0.ZU;2-P
Abstract
Methyl (S)-3-amino-3-(3-pyridyl)propanoate (2) is a key starting material i n the synthesis of RWJ-53308 (1): an orally active antagonist of the platel et fibrinogen receptor (GP IIb/IIIa antagonist). Herein, we describe an eff icient stereoselective synthesis of 2 by the hydrogenation of enantiomeric enamine 8 with Pd(OH)(2)/C, followed by the removal of the chiral auxiliary under mild conditions, a novel procedure that employs the combination of f ormic acid and triethylsilane, (C) 1999 Elsevier Science Ltd. All rights re served.