Ethyl ketone → HCID 10662297, compound

Participants

Reaction Steps

A solution of 1-(2-amino-4-methoxycarbonylphenyl)pyrrolidin-2-one (0.5 g, 2.1 mmol) from example 2, 3-pentanone (0.19 g, 2.2 mmol) and triethylamine (0.44 g, 4.3 mmol) in 10 mL of dry dichloromethane was treated with 1 m solution of titanium tetrachloride (3.5 mL, 3.5 mmol) in dichloromethane. The resulting mixture was stirred at ambient temperature for 18 h after which time sodium cyanoborohydride (0.41 g, 6.5 mmol) was added. Stirring was continued for an addition 3 h. The reaction mixture was quenched with 1 N sodium hydroxide (2 mL) and the organic layer was separated and concentrated under vacuum. The residue was extracted with ethyl acetate (3×30 mL) and the combined extracts were dried and concentrated to give an oil which was purified by column chromatography (silica gel; 10% ethanol in ether) to yield 0.16 g (25%) of 1-[4-methoxycarbonyl-2-(3-pentylamino)phenyl]pyrrolidin-2-one.

Provenance & Evidence