Process for preparing substituted phenol ethers via oxazolidine-

Details Process for preparing substituted phenol ethers via oxazolidine- Process for preparing substituted phenol ethers via oxazolidine-

1986-02-25

1988-07-26

Daus, Donald G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

548215, C07D 9306, C07D26304

Patent

active

047601825

ABSTRACT:
Phenol ethers such as 1-[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]-3-[(1-methylethyl)amino]-2-prop anol, otherwise known as betaxolol, of formula: ##STR1## 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 while the alcohol chain is elaborated. The oxazolidine ring protectant is removed by simple acid hydrolysis.

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patent: 3538150 (1970-11-01), Gilman et al.
patent: 3541130 (1970-11-01), Koppe et al.
patent: 3663607 (1972-05-01), Barrett et al.
patent: 4018778 (1977-04-01), Raabe et al.
patent: 4252984 (1981-02-01), Manoury et al.
Toran Chemical Ltd., CA 105-172044v.
Tonew et al., CA 89-190816d.

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