Acetic Acid → HCID 86586725, compound

Participants

Reaction Conditions

Reaction Steps

To (1R*,2R*,5S*,6R*)-6-amino-8-benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-1-phenyl-8-azabicyclo[3.2.1]octane (Example 108; 256 mg, 0.48 mmol) and sodium azide (75 mg, 1.15 mmol) in triethylorthoformate (0.25 ml) was added glacial acetic acid (2.5 ml) and the reaction mixture heated at 90° C. for 3 hours. The reaction mixture was cooled then concentrated in vacuo and partitioned between saturated sodium hydrogen carbonate solution and dichloromethane. The organics were dried (MgSO4) and concentrated in vacuo to give a brown oil. This was purified by flash column chromatography [5% methanol in dichloromethane] to give the title compound (66 mg, 24%).

Provenance & Evidence