Ethyl orthoformate → HCID 86586730, compound

Participants

Reaction Conditions

Reaction Steps

(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; 209 mg, 0.39 mmol) in triethylorthoformate (3.5 ml, 19.22 mmol) and glacial acetic acid (1 ml) was heated to 90° C. Sodium azide (250 mg, 3.85 mmol) was added and the mixture further heated at 90° C. overnight. The mixture was cooled and partitioned between saturated sodium hydrogen carbonate solution and dichloromethane. The organics were dried (MgSO4) and concentrated in vacuo. The reaction mixture was purified by flash column chromatography [2.5% methanol in dichloromethane] to give the title compound as a cream-coloured foam (154 mg, 56%).

Provenance & Evidence