Pyrrole → HCID 9904454, compound

Participants

Reaction Conditions

Reaction Steps

Pyrrole (0.299 ml) is dissolved in 7 ml dimethylformamide in a 25 ml one neck round bottom flask under nitrogen. The solution is cooled to 0° C., is treated with 60% sodium hydride (132 mg) and the mixture is stirred 20 minutes at room temperature. The solution is treated with (-)-5-(acetamidomethyl)-3-(3,4-difluorophenyl)-isoxazoline (Step 1, Example 11) (763 mg), and the reaction is stirred 2 hours at 50-60° C. The reaction is cooled, the dimethylformamide is removed under a stream of nitrogen, and the residue is washed with water followed by diethyl ether and is dried to give an off-white solid. The crude material is chromatographed over 25 g silica gel (230-400 mesh), eluting with 5% methanol/dichloromethane while collecting 5 ml fractions. Fractions 13-30 are combined and concentrated to give 520 mg (58%) of the title compound as a white solid, mp 176-177° C., [α]25D -73° (c 0.75).

Provenance & Evidence