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

doi:10.1016/0040-4039(95)01345-I

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 journal › Article › peer-review

132 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 language	English (US)
Pages (from-to)	6419-6422
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	36
DOIs	https://doi.org/10.1016/0040-4039(95)01345-I
State	Published - Sep 4 1995
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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@article{9f473f8f2a944bfdba48b891ed69e8fd,

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

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.",

author = "K. Rossen and Weissman, \{Steven A.\} and J. Sager and Reamer, \{R. A.\} and D. Askin and Volante, \{R. P.\} and Reider, \{P. J.\}",

year = "1995",

month = sep,

day = "4",

doi = "10.1016/0040-4039(95)01345-I",

language = "English (US)",

volume = "36",

pages = "6419--6422",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "36",

}

TY - JOUR

T1 - Asymmetric hydrogenation of tetrahydropyrazines

T2 - Synthesis of (S)-piperazine-2-tert-butylcarboxamide, an intermediate in the preparation of the HIV protease inhibitor indinavir

AU - Rossen, K.

AU - Weissman, Steven A.

AU - Sager, J.

AU - Reamer, R. A.

AU - Askin, D.

AU - Volante, R. P.

AU - Reider, P. J.

PY - 1995/9/4

Y1 - 1995/9/4

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/0029118635

UR - https://www.scopus.com/pages/publications/0029118635#tab=citedBy

U2 - 10.1016/0040-4039(95)01345-I

DO - 10.1016/0040-4039(95)01345-I

M3 - Article

AN - SCOPUS:0029118635

SN - 0040-4039

VL - 36

SP - 6419

EP - 6422

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 36

ER -

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

Abstract

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