Triethylamine → HCID 86602052, compound

Participants

Reaction Conditions

Reaction Steps

To a round bottom flask was added methylene chloride (12 mL), triethylamine (0.55 mL, 3.9 mmol), and [(S)-1-(3,5-bis-trifluoromethyl-phenyl)-ethyl]-methyl-amine (0.35 g, 1.3 mmol). The mixture was cooled to 0° C. and triphosgene (0.15 g, 0.50 mmol) in methylene chloride (4 mL) was added dropwise. The clear solution was stirred for 16 hours at room temperature. To the reaction mixture was added (2-phenyl-3-aza-bicyclo[3.1.0]hex-1-yl)-methanol (0.25 g, 1.2 mmol), diisopropyl ethyl amine (0.41 mL, 2.4 mmol), and acetonitrile (10 mL). The reaction was heated to remove the methylene chloride and then refluxed for 1 hour. The solvent was removed at reduced pressure and the residue partitioned between 0.25N HCl and methylene chloride, the organic phase was washed with saturated sodium bicarbonate solution, brine, dried over sodium sulfate, filtered, and concentrated to a quantitative yield of oil. This material was flash chromatographed on silica using a gradient of 20 to 40% EtOAc/Hexanes and the first eluted (Rf=0.39 (50% EtOAc/hexanes) spot was rechromatographed using prep TLC eluting with 5% MeOH/CHCl3 to afford the title compound as a mixture of diasteomers (0.031 g, 5.5% yield) and as an oil.

Provenance & Evidence