2, 5, 9-Trimethyl-6, 7-benzomorphan (1a) was prepared from phenylalanine (Ph) via several steps.
Ph was converted to 3- (
N-benzyl-
N-methyl) amino-4-phenyl-2-butanone (2) via Dakin-West reaction, deacetylation, acetalization, alkylation (benzylation and methylation) and deacetalization.
Reaction of (2) with 3-ethoxy-1-methylpropylmagnesium bromide afforded 2- (
N-benzyl-
N-methyl) amino-6-ethoxy-3, 4-dimethyl-1-phenyl-3-hexanol (4).
This intermediate was led to 2- (
N-benzyl-
N-methyl) amino-4- (2-ethoxyethyl) -3, 4-dimethyl-1, 2, 3, 4- tetrahydronaphthalene (6) by H
2SO
4 catalyzed dehydration followed by cyclization with AlBr
3. Debenzylation of (6) followed by cyclization with HBr gave (1).
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