Chloroform → HCID 15294933, compound

Participants

Reaction Conditions

Reaction Steps

Phosphoryl chloride (370 μl, 3.97 mmol) was added to a chloroform (6 ml)solution of N-(4,5-dimethoxy-3-hydroxyphenethyl)-4-fluorophenylacetamide (437 mg, 1.31 mmol) at room temperature, and the mixture was stirred undera nitrogen atmosphere at 55° C. for 8 hours. The solvent and the excess phosphoryl chloride were removed under reduced pressure and the resultant residue was dissolved in methanol (25 ml). Sodium borohydride (65 mg, 1.72 mmol) was added to this methanol solution under ice cooling and the mixture was stirred for 1 hour. The solvent was removed under reduced pressure, brine (50 ml) was added to the resultant residue, and the mixture was extracted three times with chloroform (30 ml). The organiclayer was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the resultant residue was recrystallized from ethyl acetate-hexane to give 199 mg (yield: 48%) of the captioned compoundas a colorless solid. Melting point: 195°-200° C. FAB-MS (m/z, (C18H20NO3F+H)+): 318 1H-NMR (300MHz, CD3OD, δ ppm): 2.97-3.08 (3H, m), 3.22-3.34 (1H, m), 3.46-3.55(2H, m), 3.78 (3H,(2H, m), 7.34-7.38 (2H, m)

Provenance & Evidence