Water → HCID 22141289, compound

Participants

Reaction Conditions

Reaction Steps

3-[3-Hexyl-6-(2,2,2-trifluoroethyl)-3-azabicyclo[3.1.0]hex-6-yl aniline (Preparation 101, 143 mg, 0.42 mmol) was dissolved in anhydrous dichloromethane (3 ml) in a dry, nitrogen-flushed flask and cooled to −12° C. in an ice/methanol bath. Pyridine (54 μl, 0.67 mmol) was added dropwise followed by methanesulfonyl chloride (39 μl, 0.50 mmol). The mixture was allowed to slowly warm to room temperature, whereupon its colour changed from yellow to bright amber. After 3 h, the mixture was treated with water (20 ml) and extracted with dichloromethane (3×20 ml). The combined organic extracts were washed with brine (20 ml), dried (MgSO4), filtered and the solvent removed in vacuo. The crude product was purified by chromatography on silica gel (5 g), eluting with hexane:ether (2:1) to give the product as an amber gum (71 mg, 40%).

Provenance & Evidence