Water → HCID 178449163, compound

Participants

Reaction Steps

To a stirred solution of amine 14 (1.3 g, 6.2 mmol) in THF (75 mL) was added 5 (1.44 g, 6.22 mmol). The reaction mixture was stirred for 1 hour, NaBH4 (329 mg, 8.71 mmol) was added followed by water (30 mL). The reaction mixture was stirred for 45 minutes then diluted with EtOAc. The mixture was washed with 1N HCl and concentrated under reduced pressure. Purification by flash chromatography (silica, 95:5:1 CH2Cl2:MeOH:NH4OH) gave 6-[trans-4-(3-phenylbutylamino)cyclohexyl]-3H-benzoxazol-2-one (640 mg, 28%), as a white solid: 1H NMR (300 MHz, DMSO-d6): δ 7.31-7.11 (m, 7H), 6.94 (s, 1H), 2,78 (m, 1H), 2.45-2.35 (m, 5H), 1.87 (br d, J=10 Hz, 2H), 1.73 (br d, J=10 Hz, 2H), 1.68 (m, 2H), 1.44 (dddd, J=10, 10, 10, 2 Hz, 2H), 1.19 (d, J=4 Hz, 3H), 1.08 (dddd, J=10, 10, 10, 2 Hz, 2H).

Provenance & Evidence