Kinetic resolution of 1-chloro-3-(1-naphthyloxy)-2-propanol, an intermediate in the synthesis of beta-adrenergic receptor blockers.
(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.
Kapoor
M
M
Biotechnology Division, Regional Research Laboratory, 180001 Jammu, India.
Anand
N
N
Koul
S
S
Chimni
S S
SS
Manhas
K S
KS
Raina
C
C
Parshad
R
R
Taneja
S C
SC
Qazi
G N
GN
D000215:Acylation; D018674:Adrenergic Antagonists / Q000138:chemical synthesis* / Q000737:chemistry*; D002175:Candida / Q000201:enzymology; D002728:Chlorohydrins / Q000737:chemistry*; D006867:Hydrolases / Q000378:metabolism; D007700:Kinetics; D008049:Lipase / Q000378:metabolism; D009089:Mucor / Q000201:enzymology; D009281:Naphthalenes / Q000737:chemistry*; D013237:Stereoisomerism
C483617:1-chloro-3-(1-naphthyloxy)-2-propanol; D018674:Adrenergic Antagonists; D002728:Chlorohydrins; D009281:Naphthalenes; D006867:Hydrolases; D008049:Lipase