Morpholine → HCID 69178046, compound

Participants

Reaction Steps

To a solution of (4-oxo-cyclohexyl)-carbamic acid tert-butyl ester (426 mg, 2.00 mmol) and morpholine (175 μL, 2.00 mmol) in CH2Cl2 (25 mL) and acetic acid (120 μL) was added sodium triacetoxyborohydride (636 mg, 3.00 mmol) and the mixture was stirred at room temperature overnight. The mixture was concentrated under reduced pressure and diluted with saturated aqueous sodium carbonate (30 mL). The aqueous layer was washed with CH2Cl2 (4×20 mL), and the combined organic extracts were dried (MgSO4), filtered, and concentrated under reduced pressure. Purification by flash column chromatography on silica gel (MeOH/CH2Cl2, 1:9) afforded the title compound as a white solid (76.2 mg, 13%). 1H NMR (CDCl3) δ 1.04-1.17 (m, 6H), 1.25-1.38 (m, 4H), 1.44 (s, 9H), 1.93 (d, 2H, J=12.0 Hz), 2.07 (d, 2H, J=12.0 Hz), 2.12-2.17 (m, 2H), 3.25-3.36 (br m, 1H), 4.35 (br m, 1H), 4.81 (br d, 1H).

Provenance & Evidence