Asymmetric hydrogenation of tetrahydropyrazines: Synthesis of (S)-piperazine-2-tert-butylcarboxamide, an intermediate in the preparation of the HIV protease inhibitor indinavir

K. Rossen, Steven A. Weissman, J. Sager, R. A. Reamer, D. Askin, R. P. Volante, P. J. Reider

Research output: Contribution to journalArticle

113 Scopus citations

Abstract

Hydrogenation of tetrahydropyrazine 4g with [(R)-BINAP(COD)Rh]TfO gave piperazine 6g in 96% yield and 99% ee. Simple hydrogenolytic deprotection and crystallization afforded the key chiral (S)-N-Boc-piperazine MK-639 intermediate 1 in high yield and enantiomeric purity.

Original languageEnglish (US)
Pages (from-to)6419-6422
Number of pages4
JournalTetrahedron Letters
Volume36
Issue number36
DOIs
StatePublished - Sep 4 1995
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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