Methanol → 4-(3,4-Dinitrobenzyl)morpholine

Participants

Reaction Conditions

Reaction Steps

Sodium borohydride (40 mg, 1.06 mmol) was placed in a nitrogen flushed flask and suspended in THF (7 mL). After the mixture was cooled to 0° C., boron trifluoride etherate (0.13 mL, 1.06 mmol) was added by syringe and followed by the addition of (3,4-dinitrophenyl)(morpholino)methanone (150 mg, 0.53 mmol) in a single portion. The suspension was stirred at room temperature for 3 h. Methanol (5 mL) was added to the reaction mixture at 0° C., and the mixture was heated at reflux for 1 h. The mixture was concentrated in vacuo and the resulting residue was partitioned between ethyl acetate (50 mL) and saturated NaHCO3 (50 mL). The organic phase was separated, washed with water (30 mL) and brine (30 mL), and dried with Na2SO4. Purification by flash chromatography (3% CH3OH/CH2Cl2) afforded the title compound (120 mg) as a solid. 1H NMR (400 MHz, CD3OD): δ 8.03 (m, 2H), 7.85 (m, 1H), 3.71 (m, 6H), 2.49 (m, 4H).

Provenance & Evidence