Water → HCID 46232856, compound

Participants

Reaction Steps

357 mg (1 mmol) 6-benzyloxy-8-(2-ethoxy-2-hydroxy-acetyl)-4H-benzo[1,4]oxazin-3-one and 217 mg (1 mmol) 1,1-dimethyl-2-(3-trifluoromethyl-phenyl)-ethylamine are stirred for 3 hours in 5 mL ethanol at 65° C. The mixture is cooled to ambient temperature, 113 mg (3 mmol) of sodium borohydride are added and the mixture is stirred overnight. It is combined with 2 mL water, stirred for 30 minutes and then diluted with 10 mL dichloromethane. The solution is filtered through kieselguhr and washed with dichloromethane. The eluate is freed from solvent and the residue is dissolved in 5 mL ethanol and hydrogenated at 2.5 bar and ambient temperature with palladium on charcoal (10%) as catalyst. Then the catalyst is separated off and the crude product is purified by chromatography (reverse phase, acetonitrile/water gradient with 0.1% trifluoroacetic acid). Beige solid. Yield: 169 mg (31%, trifluoroacetate); mass spectroscopy: [M+H]+=425.

Provenance & Evidence