Trimethylamine oxide dihydrate → 6,7,8,9-Tetrahydro-5H-6,9-methanocyclohepta[b]pyridine-7,8-diol

Participants

Reaction Steps

A mixture of 3-azatricyclo[7.2.1.02,7]dodeca-2,4,6,10-tetraene (Preparation 25, 0.96 g, 6.11 mmol), trimethylamine N-oxide dihydrate (0.75 g, 6.73 mmol) and osmium tetroxide (2.5 wt % solution in 2-methyl-2-propanol, 2 □l) in dichloromethane (15 ml) were stirred for 18 h. A further portion of osmium tetroxide (2.5 wt % solution in 2-methyl-2-propanol, ca. 1 □l) was added and the reaction mixture was stirred for a further 18 h. The reaction mixture was subjected to chromatography eluting with hexane and then ethyl acetate to give the title compound as a solid (1.16 g, 100%).

Provenance & Evidence