New method for the preparation of (R)-carnitine

Choong Eui Song; Jae Kyun Lee; So Ha Lee; Sang gi Lee

doi:10.1016/0957-4166(95)00125-9

New method for the preparation of (R)-carnitine

Choong Eui Song, Jae Kyun Lee, So Ha Lee, Sang gi Lee

Department of Chemistry & Nanoscience

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

42 Scopus citations

Abstract

A new method for the preparation of (R)-carnitine (1) has been developed from enantiomerically pure (R)-4-(trichloromethyl)-oxetan-2-one [(R)-2] which was easily obtained from the [2+2]-cycloaddition of ketene and chloral in the presence of catalytic amounts of poly(acryloyl quinidine). The key intermediate, ethyl (R)-3-hydroxy-4-chlorobutyrate[(R)-5], was prepared by ethanolysis of (R)-2 followed by selective bis-dechlorination of ethyl (R)-3-hydroxy-4,4,4-trichlorobutyrate [(R)-3].

Original language	English
Pages (from-to)	1063-1066
Number of pages	4
Journal	Tetrahedron Asymmetry
Volume	6
Issue number	5
DOIs	https://doi.org/10.1016/0957-4166(95)00125-9
State	Published - May 1995

Bibliographical note

Funding Information:
Acknowledgement: This research was supported by grant from Ministry of Science and Technology in Korea.

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title = "New method for the preparation of (R)-carnitine",

abstract = "A new method for the preparation of (R)-carnitine (1) has been developed from enantiomerically pure (R)-4-(trichloromethyl)-oxetan-2-one [(R)-2] which was easily obtained from the [2+2]-cycloaddition of ketene and chloral in the presence of catalytic amounts of poly(acryloyl quinidine). The key intermediate, ethyl (R)-3-hydroxy-4-chlorobutyrate[(R)-5], was prepared by ethanolysis of (R)-2 followed by selective bis-dechlorination of ethyl (R)-3-hydroxy-4,4,4-trichlorobutyrate [(R)-3].",

author = "Song, {Choong Eui} and Lee, {Jae Kyun} and Lee, {So Ha} and Lee, {Sang gi}",

note = "Funding Information: Acknowledgement: This research was supported by grant from Ministry of Science and Technology in Korea.",

year = "1995",

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doi = "10.1016/0957-4166(95)00125-9",

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journal = "Tetrahedron Asymmetry",

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T1 - New method for the preparation of (R)-carnitine

AU - Song, Choong Eui

AU - Lee, Jae Kyun

AU - Lee, So Ha

AU - Lee, Sang gi

N1 - Funding Information: Acknowledgement: This research was supported by grant from Ministry of Science and Technology in Korea.

PY - 1995/5

Y1 - 1995/5

N2 - A new method for the preparation of (R)-carnitine (1) has been developed from enantiomerically pure (R)-4-(trichloromethyl)-oxetan-2-one [(R)-2] which was easily obtained from the [2+2]-cycloaddition of ketene and chloral in the presence of catalytic amounts of poly(acryloyl quinidine). The key intermediate, ethyl (R)-3-hydroxy-4-chlorobutyrate[(R)-5], was prepared by ethanolysis of (R)-2 followed by selective bis-dechlorination of ethyl (R)-3-hydroxy-4,4,4-trichlorobutyrate [(R)-3].

AB - A new method for the preparation of (R)-carnitine (1) has been developed from enantiomerically pure (R)-4-(trichloromethyl)-oxetan-2-one [(R)-2] which was easily obtained from the [2+2]-cycloaddition of ketene and chloral in the presence of catalytic amounts of poly(acryloyl quinidine). The key intermediate, ethyl (R)-3-hydroxy-4-chlorobutyrate[(R)-5], was prepared by ethanolysis of (R)-2 followed by selective bis-dechlorination of ethyl (R)-3-hydroxy-4,4,4-trichlorobutyrate [(R)-3].

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DO - 10.1016/0957-4166(95)00125-9

M3 - Article

AN - SCOPUS:0029052235

SN - 0957-4166

VL - 6

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EP - 1066

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 5

ER -

New method for the preparation of (R)-carnitine

Abstract

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