1,8-Diazabicyclo(5.4.0)undec-7-ene → (4S,6S)-4-(5-bromo-2-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine

Participants

Reaction Conditions

Reaction Steps

A solution of N-((4S,6S)-4-(5-bromo-2-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)benzamide (4 g, 789 mg, 1.718 mmol) in anhydrous MeOH (20 mL) was treated with 1,8-diazabicyclo-[5.4.0]undec-7-ene (Aldrich; 311 μL, 2.063 mmol) and heated to 65° C. for 16 h. The reaction mixture was concentrated and extracted into EtOAc from saturated aqueous NH4Cl. The organic extract was dried over MgSO4, concentrated, and purified by flash chromatography on silica gel (Gradient: 0%→50% EtOAc/hexane) to give (4S,6S)-4-(5-bromo-2-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine (585 mg, 1.647 mmol) as a white foam. MS m/z=355 M+. Calculated for C12H11BrF4N2O: 355.1

Provenance & Evidence