Crystallization-induced diastereoselection: asymmetric synthesis of substance P inhibitors

Philip J Pye; Kai Rossen; Steven A Weissman; Ashok Maliakal; Robert A Reamer; Richard Ball; Nancy N Tsou; R P Volante; Paul J Reider

doi:10.1002/1521-3765(20020315)8:6<1372::aid-chem1372>3.0.co;2-6

Crystallization-induced diastereoselection: asymmetric synthesis of substance P inhibitors

Chemistry. 2002 Mar 15;8(6):1372-6. doi: 10.1002/1521-3765(20020315)8:6<1372::aid-chem1372>3.0.co;2-6.

Authors

Philip J Pye¹, Kai Rossen, Steven A Weissman, Ashok Maliakal, Robert A Reamer, Richard Ball, Nancy N Tsou, R P Volante, Paul J Reider

Affiliation

¹ Department of Process Research, Merck Research Laboratories, P.O. Box 2000, Rahway, New Jersey 07065, USA. [email protected]

PMID: 11921220
DOI: 10.1002/1521-3765(20020315)8:6<1372::aid-chem1372>3.0.co;2-6

Abstract

A novel three-component condensation followed by a crystallization-induced asymmetric transformation is used to build this key substance P inhibitor intermediate in a short synthetic sequence.

MeSH terms

Animals
Antidepressive Agents / chemical synthesis*
Crystallization
Humans
Hydroxylation
Molecular Structure
Morpholines / chemical synthesis*
Stereoisomerism
Substance P / antagonists & inhibitors*
Triazoles / chemical synthesis*

Substances

2-(4-fluorophenyl)-1-(3-oxo-(2H,4H)-1,2,4-triazol-5-ylmethyl)-3-(1-(3,5-bis(trifluoromethyl)phenyl)ethoxy)morpholine
Antidepressive Agents
Morpholines
Triazoles
Substance P