Methanol → (1R*,2R*,5S*,6R*)-8-Benzyl-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]octan-2-ol

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Reaction Steps

(1R*,5S*,6R*)-8-Benzyl-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]octan-2-one (Description 3; 3.05 g, 7.03 mmol) was dissolved in hot THF (10 ml) and methanol (150 ml) was added. The mixture was heated at reflux for 2 minutes and cooled to +5° C. Sodium borohydride (600 mg, 15.8 mmol) was added. The reaction mixture was stirred for 20 minutes at +5° C. The cooling bath was removed and the mixture was stirred for 90 minutes at ambient temperature. Saturated aqueous NaHCO3 (10 ml) was added and the mixture was concentrated in vacuo. The residue was treated with water and extracted with ethyl acetate (3×50 ml). The combined organic extracts were dried (Na2SO4) and concentrated. The solid residue was crystallised from acetone:iso-hexane to give the title compound (2.95 g, 97%) as white crystals.

Provenance & Evidence