title: Kinetic resolution of 1-chloro-3-(1-naphthyloxy)-2-propanol, an intermediate in the synthesis of beta-adrenergic receptor blockers.
abstract: (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.
authors.affiliation: Biotechnology Division, Regional Research Laboratory, 180001 Jammu, India.
authors.forename: M
authors.initials: M
authors.lastname: Kapoor
authors.forename: N
authors.initials: N
authors.lastname: Anand
authors.forename: S
authors.initials: S
authors.lastname: Koul
authors.forename: S S
authors.initials: SS
authors.lastname: Chimni
authors.forename: K S
authors.initials: KS
authors.lastname: Manhas
authors.forename: C
authors.initials: C
authors.lastname: Raina
authors.forename: R
authors.initials: R
authors.lastname: Parshad
authors.forename: S C
authors.initials: SC
authors.lastname: Taneja
authors.forename: G N
authors.initials: GN
authors.lastname: Qazi
mesh_terms: 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
chemical_list: C483617:1-chloro-3-(1-naphthyloxy)-2-propanol; D018674:Adrenergic Antagonists; D002728:Chlorohydrins; D009281:Naphthalenes; D006867:Hydrolases; D008049:Lipase