Potassium Carbonate → HCID 9818557, compound

Participants

Reaction Conditions

Reaction Steps

To a resealable tube containing (+/-)-N-[[4,5-dihydro-3-(3,4-difluorophenyl)-5-isoxazolyl]methyl]acetamide (Step 3, Example 3) (1.70 g) in morpholine (5.83 mL) is added potassium carbonate (1.16 g) and heated to 140° C. for 48 hours. The reaction is diluted with CH2Cl2 (50 mL) and washed with H2O (3×50 mL) and saline (50 mL). The organic phase is dried over sodium sulfate, concentrated in vacuo and chromatographed on silica gel (230-400 mesh), eluting with methylene chloride/methanol (98.5/1.5). The appropriate fractions are combined (Rf =0.30, TLC, chloroform/methanol, 95/5) and concentrated in vacuo to give the title compound. The racemic material is separated on chiral HPLC (Chiralpak AD column, eluting with 8:2:1.5 heptane/isopropanol/chloroform) to give the individual enantiomers, the title compound having mp 179-180° C., [α]25D -71° (DMSO).

Provenance & Evidence