An asymmetric synthesis of the novel H3 agonist (+)-(3R,4R)-3-(4-imidazolyl)-4-methylpyrrolidine dihydrochloride (Sch 50971)

被引：22

作者：

Aslanian, R

Lee, G

Iyer, RV

Shih, NY

Piwinski, JJ

Draper, RW

McPhail, AT

机构：

[1] Schering Plough Corp, Res Inst, Dept Chem Proc Dev, Kenilworth, NJ 07033 USA

[2] Schering Plough Corp, Res Inst, Dept Chem Res, Kenilworth, NJ 07033 USA

[3] Duke Univ, Dept Chem, Paul M Gross Chem Lab, Durham, NC 27708 USA

来源：

TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 19期

关键词：

D O I：

10.1016/S0957-4166(00)00380-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A short, high yielding, enantioselective synthesis of the novel H-3 agonist Sch 50971 1 is described. The key enantiodifferentiating step is the 1,4-addition of a chiral N-propionyloxazolidinone to a nitroolefin. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：3867 / 3871

页数：5

相关论文

共 15 条

[1] ASYMMETRIC MICHAEL-ADDITIONS - STEREOSELECTIVE ALKYLATION OF CHIRAL, NON-RACEMIC ENOLATES BY NITROOLEFINS - PREPARATION OF ENANTIOMERICALLY PURE GAMMA-AMINOBUTYRIC AND SUCCINIC ACID-DERIVATIVES [J].

CALDERARI, G ;

SEEBACH, D .

HELVETICA CHIMICA ACTA, 1985, 68 (06) :1592-1604

[2]

CHASTANET J, 1992, HETEROCYCLES, V34, P1565

[3] ASYMMETRIC NITROALKENE [4+2] CYCLOADDITIONS - ENANTIOSELECTIVE SYNTHESIS OF 3-SUBSTITUTED AND 3,4-DISUBSTITUTED PYRROLIDINES [J].

DENMARK, SE ;

MARCIN, LR .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (10) :3221-3235

[4] ENANTIOSELECTIVE MICHAEL REACTIONS - DIASTEREOSELECTIVE REACTIONS OF CHLOROTITANIUM ENOLATES OF CHIRAL N-ACYLOXAZOLIDINONES WITH REPRESENTATIVE ELECTROPHILIC OLEFINS [J].

EVANS, DA ;

BILODEAU, MT ;

SOMERS, TC ;

CLARDY, J ;

CHERRY, D ;

KATO, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5750-5752

[5]

Hey JA, 1998, ARZNEIMITTEL-FORSCH, V48, P881

[6]

Hill SJ, 1997, PHARMACOL REV, V49, P253

[7] HETEROCYCLES IN ASYMMETRIC-SYNTHESIS .1. CONSTRUCTION OF THE CHIRAL BUILDING-BLOCKS FOR ENANTIOSELECTIVE ALKALOID SYNTHESIS VIA AN ASYMMETRIC INTRAMOLECULAR MICHAEL REACTION [J].

HIRAI, Y ;

TERADA, T ;

YAMAZAKI, T ;

MOMOSE, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (04) :509-516

[8] MOLECULAR PHARMACOLOGICAL ASPECTS OF HISTAMINE-RECEPTORS [J].

LEURS, R ;

SMIT, MJ ;

TIMMERMAN, H .

PHARMACOLOGY & THERAPEUTICS, 1995, 66 (03) :413-463

[9]

Leurs R, 1995, Prog Drug Res, V45, P107

[10] Therapeutic potential histamine H3 receptor agonists and antagonists [J].

Leurs, R ;

Blandina, P ;

Tedford, C ;

Timmerman, H .

TRENDS IN PHARMACOLOGICAL SCIENCES, 1998, 19 (05) :177-183