Dimethylformamide → HCID 87367896, compound

Participants

Reaction Conditions

Reaction Steps

A solution of EXAMPLE 40B (0.4 g, 1.5 mmol)) in tetrahydrofuran (5 mL) was cooled to −78° C. and treated with a 1.3 M solution of sec-butyl lithium in cyclohexane (1.8 mL, 2.3 mmol). The mixture was stirred for 30 minutes at −78° C. and treated with N,N′-dimethylformamide (0.4 mL, 5.2 mmol). The mixture was warmed to ambient temperature over 1.5 hours, acetic acid (1 mL) added and the mixture stirred at ambient temperature for 10 minutes. Water (2 mL) was added and the mixture diluted with ethyl acetate. The organic layer was separated, washed with saturated sodium bicarbonate, water and brine, and concentrated. The residue was purified by flash chromatography on silica gel using 10-60% hexane/ethyl acetate to give the title compound (0.135 g, 42%). MS (ESI) m/e 218 (M+H)+.

Provenance & Evidence