Triethylamine → HCID 20810193, compound

Participants

Reaction Steps

780 mg (3.668 mmol) of (2R)-methyl-3-oxo-6-aminomethyl-2H-1,4-benzoxazine-hydrochloride, 462.4 mg (3.668 mmol) of 4,4,4-trifluorobutyraldehyde and 371.2 mg (3.668 mmol) of triethylamine are dissolved in a mixture that consists of methanol and tetrahydrofuran (4:1). After three hours of stirring at room temperature, 75.2 mg of sodium borohydride is added. After stirring overnight at room temperature, the batch is added to water and shaken three times with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution, dried and spun in. After chromatography on silica gel (mobile solvent: dichloromethane/isopropanol, 608.8 mg (55%) of the desired compound is obtained.

Provenance & Evidence