Practical synthesis of Boc-protected cis-4-trifluoromethyl and cis-4-difluoromethyl-L- prolines

Xiao-Long Qiu; Feng-Ling Qing

doi:10.1021/jo0257400

Practical synthesis of Boc-protected cis-4-trifluoromethyl and cis-4-difluoromethyl-L- prolines

J Org Chem. 2002 Oct 4;67(20):7162-4. doi: 10.1021/jo0257400.

Authors

Xiao-Long Qiu¹, Feng-Ling Qing

Affiliation

¹ Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.

PMID: 12354018
DOI: 10.1021/jo0257400

Abstract

A short, efficient, and diastereomerically pure synthesis of N-Boc-cis-4-trifluoromethyl-L-proline (7) and N-Boc-cis-4-difluoromethyl-L-proline (9) from N-Boc-4-oxo-L-proline (4) is described. The reaction of 4 with Me(3)SiCF(3) and the conversion of the carbonyl group of 4 into the difluoromethylene group are the key steps for the synthesis of 7 and 9, respectively.

MeSH terms

Chromatography, High Pressure Liquid
Combinatorial Chemistry Techniques*
Crystallography, X-Ray
Magnetic Resonance Spectroscopy
Molecular Structure
Proline* / analogs & derivatives
Proline* / chemical synthesis
Proline* / chemistry
Stereoisomerism

Substances

N-tert-butoxycarbonyl-4-difluoromethylproline
N-tert-butoxycarbonyl-4-trifluoromethylproline
benzyl N-tert-butoxycarbonyl-4-oxo-prolinate
Proline