Sodium hydride → HCID 9905524, compound

Participants

Reaction Conditions

Reaction Steps

3-Formylpyrrole (628 mg) is dissolved in 12 ml dimethylformamide in a 50 ml one neck round bottom flask under nitrogen. The solution is cooled to 0° C., is treated with 60% sodium hydride (554 mg), and the mixture is stirred 30 minutes at room temperature. The solution is treated with (-)-5-(acetamidomethyl)-3-(3,4-difluorophenyl)-isoxazoline (Step 1, Example 11) (1.52 g), and the reaction is stirred 6 hours at 65° C. The reaction is cooled, is diluted with 100 ml ethyl acetate, and is washed with 4×25 ml 50% saturated sodium chloride. The organics are dried over anhydrous potassium carbonate and are concentrated in vacuo to a yellow oil. The crude material is chromatographed over 75 g silica gel (230-400 mesh) eluting with 3% methanol/dichloromethane and after a 200 ml forerun collecting 9 ml fractions. Fractions 48-69 are combined and concentrated to give 1.10 g (56%) of the title compound as a white solid, mp 155-156° C., [α]25D -69° (c 0.61, ethanol).

Provenance & Evidence