Methanol → HCID 131729367, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-amino-5-[(3aR*,7S*,7aS*)-3-(3-tert-butyl-benzyl)-2,5,5-trioxo-octahydro-1-oxa-5lambda*6*-thia-3-aza-inden-7-ylmethyl]-3-fluoro-benzaldehyde (0.12 g, 0.245 mmol) in CH2Cl2-MeOH 2:1 (3 mL) was added a 2M solution of ethylamine in MeOH (0.18 mL, 0.397 mmol). After stirring for 3 h at 25° C. the pH was adjusted to 4 with AcOH and the imine was reduced with NaBH3CN (0.027 g 85%, 0.367 mmol). After 20 min the reaction mixture was basified with saturated K2CO3 solution and extracted with EtOAc. Combined organic layers were washed with water and brine, dried over MgSO4, filtered and evaporated. The title compound was obtained after flash-chromatography on silica gel (CH2Cl2 to CH2Cl2-MeOH 20:1) as a beige solid: TLC (CH2Cl2-MeOH 19:1) Rf=0.39; ESIMS [M+H]+=517.

Provenance & Evidence