SYNTHESIS OF 8-AZA-D-HOMO-18-NORESTRONE METHYL ETHER
- 1 May 1965
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 43 (5) , 1323-1328
- https://doi.org/10.1139/v65-180
Abstract
Alkylation of the potassium salt of 1,4-dihydro-2,6-dimethoxybenzene with 2-(2-bromoethyl)piperidine yielded the bis-enol ether I, which, on acid hydrolysis, afforded the crystalline vinylogous amide II. Lithium aluminium hydride reduction of II gave two isomers of 1,2,3,4,4a,5,6,6a,8,9,10,10a-dodecahydro-7H-benzo[c]quinolizin-7-one (III). A similar series of reactions starting with 1-(2-chloroethyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (V) gave two isomers of 2,3,4,4a, 6,7,11b,12,13,13a-decahydro-9-methoxy-1H-di-benzo[a,f]quinolizin-1-one (8-aza-D-homo-18-norestrone methyl ether) (IX).Keywords
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