Preparation of phenol ethers using cyclic intermediates

Details Preparation of phenol ethers using cyclic intermediates Preparation of phenol ethers using cyclic intermediates

C - Chemistry, Metallurgy

07

D

260/604.2, 260/3

C07D 263/06 (2006.01) C07C 93/14 (1985.01)

Patent

CA 1265523

ABSTRACT OF THE DISCLOSURE Phenol ethers such as 1-[4-[2-(cyclopropylmethoxy)- ethyl]phenoxy]-3-((1-methylethyl)amino]-2-propanol, otherwise known as betaxolol, of formula: Image are prepared from p-hydroxyphenethyl alcohol by first reacting at the phenolic group, with epichlorohydrin followed by isopropylamine, to prepare the required secondary amine-hydroxy side chain. Protection of the alcoholic group is not required during these steps. Then the secondary amine-alcohol group is protected by reaction with a suitable aldehyde such as benzaldehyde to form an oxazolidine ring protectant whilst the alcohol chain is elaborated. The oxazolidine ring protectant is removed by simple acid hydrolysis. The phenol ether products have pharmaceutical utility, e.g. as B-adrenergic blocking agents.

473827

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