Hydrochloric Acid → HCID 59261034, compound

Participants

Reaction Conditions

Reaction Steps

A solution of DMSO (0.656 mL, 9.24 mmol) in 7 mL of DCM was added dropwise to a cooled (−78° C.) solution of oxalyl chloride (0.403 mL, 4.62 mmol) in 30 mL of DCM. After 5 min, a solution of (3S)-3-isopropyl-3-{[6-(trifluoromethyl)-2H-1,3-benzoxazin-3(4H)-yl]carbonyl}cyclopentanol (826 mg, 2.31 mmol) in 8 mL of DCM was added dropwise. The reaction mixture was stirred at −78° C. for 25 min, then was treated dropwise with neat triethylamine (2.58 mL, 18.5 mmol). After stirring at −78° C. for an additional 10 min, the reaction mixture was allowed to warm to rt and stir for 1.5 h. The mixture was then poured into 1N HCl solution and extracted with DCM. The organic layer was washed with more 1N HCl solution, then with saturated NaHCO3 solution and brine. The organic layer was then dried over anhydrous MgSO4, filtered, and concentrated. The crude product was purified by MPLC (silica, 75% ethyl acetate/hexanes) to provide (3S)-3-isopropyl-3-{[6-(trifluoromethyl)-2H-1,3-benzoxazin-3(4H)-yl]carbonyl}cyclopentanone.

Provenance & Evidence