A convenient method for synthesis of trans-4-cyclohexyl-L-proline

Xiao Chen; Da Ming Du; Wen Ting Hua

doi:10.1016/S0957-4166(02)00052-6

A convenient method for synthesis of trans-4-cyclohexyl-L-proline

Xiao Chen, Da Ming Du, Wen Ting Hua^*

^*Corresponding author for this work

Peking University

Research output: Contribution to journal › Article › peer-review

14 Citations (Scopus)

Abstract

A convenient method for the synthesis of the fosinopril precursor, trans-4-cyclohexyl-L-proline 1, has been developed. A highly stereoselective alkylation of N-benzyl-pyroglutamic acid 2 with 3-bromocyclohexene at -10°C and subsequent hydrogenolysis afforded the trans-4-cyclohexyl-L-pyroglutamic acid 4. The esterified 4 was sulfurized with Lawesson's reagent, desulfurized with Raney-Ni and hydrogenolytic cleavage of the benzyl protecting groups to afford 1 with 93% e.e.

Original language	English
Pages (from-to)	43-46
Number of pages	4
Journal	Tetrahedron Asymmetry
Volume	13
Issue number	1
DOIs	https://doi.org/10.1016/S0957-4166(02)00052-6
Publication status	Published - 13 Feb 2002
Externally published	Yes

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title = "A convenient method for synthesis of trans-4-cyclohexyl-L-proline",

abstract = "A convenient method for the synthesis of the fosinopril precursor, trans-4-cyclohexyl-L-proline 1, has been developed. A highly stereoselective alkylation of N-benzyl-pyroglutamic acid 2 with 3-bromocyclohexene at -10°C and subsequent hydrogenolysis afforded the trans-4-cyclohexyl-L-pyroglutamic acid 4. The esterified 4 was sulfurized with Lawesson's reagent, desulfurized with Raney-Ni and hydrogenolytic cleavage of the benzyl protecting groups to afford 1 with 93% e.e.",

author = "Xiao Chen and Du, {Da Ming} and Hua, {Wen Ting}",

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T1 - A convenient method for synthesis of trans-4-cyclohexyl-L-proline

AU - Chen, Xiao

AU - Du, Da Ming

AU - Hua, Wen Ting

PY - 2002/2/13

Y1 - 2002/2/13

N2 - A convenient method for the synthesis of the fosinopril precursor, trans-4-cyclohexyl-L-proline 1, has been developed. A highly stereoselective alkylation of N-benzyl-pyroglutamic acid 2 with 3-bromocyclohexene at -10°C and subsequent hydrogenolysis afforded the trans-4-cyclohexyl-L-pyroglutamic acid 4. The esterified 4 was sulfurized with Lawesson's reagent, desulfurized with Raney-Ni and hydrogenolytic cleavage of the benzyl protecting groups to afford 1 with 93% e.e.

AB - A convenient method for the synthesis of the fosinopril precursor, trans-4-cyclohexyl-L-proline 1, has been developed. A highly stereoselective alkylation of N-benzyl-pyroglutamic acid 2 with 3-bromocyclohexene at -10°C and subsequent hydrogenolysis afforded the trans-4-cyclohexyl-L-pyroglutamic acid 4. The esterified 4 was sulfurized with Lawesson's reagent, desulfurized with Raney-Ni and hydrogenolytic cleavage of the benzyl protecting groups to afford 1 with 93% e.e.

UR - http://www.scopus.com/inward/record.url?scp=0037070074&partnerID=8YFLogxK

U2 - 10.1016/S0957-4166(02)00052-6

DO - 10.1016/S0957-4166(02)00052-6

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JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 1

ER -

A convenient method for synthesis of trans-4-cyclohexyl-L-proline

Abstract

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