Methanol → HCID 69890918, compound

Participants

Reaction Steps

(1R*,5S*,6S*)-8-Benzyl-6-(tert-butoxycarbonyl)-1-phenyl-8-azabicyclo[3.2.1]octan-2-one (Description 19b; 750 mg, 1.91 mmol) was dissolved in THF (5 ml) and methanol (25 ml) was added. The mixture was cooled to +5° C. and treated with sodium borohydride (184 mg, 4.8 mmol). The reaction mixture was stirred for 45 minutes, quenched with saturated aqueous NH4Cl (10 ml) and concentrated in vacuo. The aqueous residue was extracted with dichloromethane. The combined organic extracts were dried (Na2SO4) and concentrated to give crude product as a 10:1 mixture of diastereoisomers. The residue was purified by chromatography on silica gel (iso-hexane:diethyl ether 0-30%) to give the (1R*,2R*,5S*,6S*)-isomer (710 mg, 92%) and the (1R*,2S*,5S*,6S*)-isomer (59 mg, 8%) of the title compound.

Provenance & Evidence