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Kinetic resolution of 1-chloro-3-(1-naphthyloxy)-2-propanol, an intermediate in the synthesis of beta-adrenergic receptor blockers.

IR@IIIM: CSIR-Indian Institute of Integrative Medicine, Jammu

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Title Kinetic resolution of 1-chloro-3-(1-naphthyloxy)-2-propanol, an intermediate in the synthesis of beta-adrenergic receptor blockers.
 
Creator Kapoor, M
Anand, N
Koul, S
Chimni, S S
Manhas, K S
Raina, C
Parshad, R
Taneja, S C
Qazi, G N
 
Subject Chemical Sciences
 
Description (R)- and (S)-1-chloro-3-(1-naphthyloxy)-2-propanol are intermediates in the synthesis of beta-adrenergic blocking agents and antihypertensive drugs such as propranolol and nadoxolol. Herein, improvement in the preparation of racemic 1-chloro-3-(1-naphthyloxy)-2-propanol generated from 1-naphthol and epichlorohydrin are reported. In addition, kinetic resolution studies have been conducted to obtain both (R) and (S)-1-chloro-3-(1-naphthyloxy)-2-propanol. These compounds were obtained in highly optically pure form by the stereoselective hydrolysis of its acyl derivatives using whole cell preparations containing enzymes from native sources. The results were compared with those obtained using commercial lipases.
 
Date 2003-06
 
Type Article
PeerReviewed
 
Format application/pdf
 
Identifier http://iiim.csircentral.net/402/1/10.1016%2DS0045%2D2068(03)00050%2D6.pdf
Kapoor, M and Anand, N and Koul, S and Chimni, S S and Manhas, K S and Raina, C and Parshad, R and Taneja, S C and Qazi, G N (2003) Kinetic resolution of 1-chloro-3-(1-naphthyloxy)-2-propanol, an intermediate in the synthesis of beta-adrenergic receptor blockers. Bioorganic chemistry, 31 (3). pp. 259-69. ISSN 0045-2068
 
Relation http://iiim.csircentral.net/402/