Sodium borohydride → HCID 22728863, compound

Participants

Reaction Steps

2,3-Dihydro-4H-1,4-benzoxazin-4-amine hydrochloride (0.0830 g, 0.444 mmol) and 1-trifluoroacetyl-3-methylpiperidin-4-one (0.0929 g, 0.444 mmol) were combined in 2-propanol (3.75 mL) and stirred at reflux for 3.75 hours under N2. The reaction mixture was cooled to room temperature, NaBH4 (0.0523 g, 1.38 mmol) was added and the reaction mixture was refluxed for 1 hour under N2. The cooled reaction mixture was quenched with CH3OH (2 mL) and partitioned between CH2Cl2 and H2O. The layers were separated and the aqueous layer was extracted with CH2Cl2. The combined CH2Cl2 extracts were washed with H2O, dried over Na2SO4, filtered and concentrated to yield crude 8-trifluoroacetyl-6b-methyl-1,2,6b,7,8,9,10,10a-octahydro[1,4]oxazino[2,3,4-hi]pyrido[4,3-b]indole (0.130 g). MS (ESI+) for C16H17F3N2O2 m/z 327.0 (M+H)+.

Provenance & Evidence