Acetone → 3-Benzyldecahydro-1,5-methanocyclopenta[d]azepine-6,7-diol

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A solution of 9-(phenylmethyl)-9-azatricyclo[5.3.1.02,6]undec-3-ene (Preparation 35, 6.7 g, 28.0 mmol), N-methylmorpholine N-oxide (3.45 g, 29.45 mmol) and osmium tetroxide (2.5 wt % in 2-methyl-2-propanol, 2 □l) in acetone (50 ml) was stirred for 18 h. Florisil and aqueous sodium hydrogensulfite (4 ml) were added and the reaction mixture was stirred for 30 min and filtered. Methanol (50 ml) was added and the reaction mixture was concentrated to give an oil which was purified by flash chromatography eluting with ethyl acetate:hexane (50:50) to give an oil (6.2 g, 80%) which crystallises upon standing.

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