100835-75-4Relevant academic research and scientific papers
The Reduction of Tertiary N-Styrylenamides
Ainscow, R. Barry,Brettle, Roger,Shibib, Sa'ad M.
, p. 1781 - 1786 (2007/10/02)
Magnesium and methanol reduction of N,9-dibenzyl-8-azabicyclonon-1(6)-en-7-one (6) gave all four racemates of N,9-dibenzyl-8-azabicyclononan-7-one (1)-(4), with a 13:6 ratio of cis-fused to trans-fused products.Selective reduction of N,9-dibenzyl-8-azabicyclonon-1(6),3-dien-7-one (5) gave almost exclusively the two cis-fused racemates of N,9-dibenzyl-8-azabicyclonon-3-en-7-one (9) and (10).Magnesium and methanol did not reduce (E)-N-benzyl-9-benzylidene-cis-bicyclononan-7-one (7) and (E)-N-benzyl-N-(1-methyl-2-phenylvinyl)-acetamide (16a), but did reduce (E)-N-benzyl-N-styrylacetamide (16b) and (E)- and (Z)-N-styrylpyrrolidin-2-one (13) and (14); incomplete reduction of (Z)-N-benzyl-N-(1-methyl-2-phenylvinyl)-acetamide (15a) and (Z)-N-benzyl-N-styrylacetamide (15b) was observed.Reduction does not occur when the styryl phenyl group is twisted out of conjugation.Sodium and liquid ammonia reduction of (E)-N-benzyl-9-benzylidene-cis-8-azabicyclononan-7-one (7) gave (1RS,6SR,9RS)-9-benzyl-8-azabicyclononan-7-one and N-benzyl-2-(2-phenylethyl)cyclohexane-1-carboxamide (20).A similar cleavage of the β-styryl-nitrogen bond was observed in the reduction of (Z)-N-benzyl-N-(1-methyl-2-phenylvinyl)acetamide (15a), but not with (E)-N-styrylpyrrolidin-2-one (13).Several tertiary N-styrylenamides were not reduced by sodium cyanoborohydride in acetic acid but N-benzyl-9-benzylidene-cis-8-azabicyclonon-3-en-7-one (8) and N-benzyl-9-benzylidene-cis-8-azabicyclononan-7-one (7) gave (1RS,6SR,9RS)-N,9-dibenzyl-8-azabicyclonon-3-en-7-one (9) and (1RS,6SR,9RS)-N,9-dibenzyl-8-azabicyclononan-7-one (2) respectively.
