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

Temperature

0 °C

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).

1. temperaturethe mixture was heated
2. temperatureat reflux for 1 h
3. concentrationThe mixture was concentrated in vacuo
4. customthe resulting residue was partitioned between ethyl acetate (50 mL) and saturated NaHCO3 (50 mL)
5. customThe organic phase was separated
6. washwashed with water (30 mL) and brine (30 mL)
7. dry with materialdried with Na2SO4
8. customPurification by flash chromatography (3% CH3OH/CH2Cl2)

ORD record

ord-56509d9c3f8b46968361243ce3eaa5bf

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08569511B2