Sodium Azide → HCID 86586727, compound

Participants

Reaction Steps

(1R*,2R*,5S*,6R*)-6-Acetamido-8-benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-1-phenyl-8-azabicyclo[3.2.1]octane (Example 109; 384 mg, 0.67 mmol) and sodium azide in dichloromethane (10 ml) were cooled to 0° C. and trifluoromethanesulphonic anhydride (0.11 ml, 0.67 mmol) added. The reaction was warmed to room temperature and stirred for 3 hours then quenched with saturated sodium hydrogen carbonate solution and extracted with dichloromethane (×3). The organics were dried (MgSO4) and concentrated in vacuo to give a brown solid. This was purified by flash column chromatography [2.5% methanol in dichloromethane] to give the title compound as a cream-coloured solid (134 mg, 34%).

Provenance & Evidence