Ethyl Acetate → racemic 2,6-difluoro-N-[(1R,2R,3R)-2-(4-fluorophenyl)-3-methyl-cyclopropyl]benzamide

Participants

Reaction Conditions

Reaction Steps

4-Fluorophenyl benzaldehyde-tosylhydrazone sodium salt from example P2b (261 mg, 0.832 mmol), 2,6-difluoro-N—[(Z)-prop-1-enyl]benzamide (164 mg, 832 mmol), benzyltriethylammonium chloride (18.6 mg, 0.083 mmol), and rhodium acetate dimer (3.6 mg, 0.0083 mmol) were stirred with dioxane (6 ml) to give a thick slurry. This was heated at 75° C. for 4 hours. The mixture was shaken between EtOAc and water. The organic phase was dried with MgSO4 and evaporated to yield 230 mg of a crude mixture. This was chromatographed on silica with EtOAc/cyclohexane to yield 26 mg (10%) of racemic 2,6-difluoro-N-[(1R,2R,3R)-2-(4-fluorophenyl)-3-methyl-cyclopropyl]benzamide. M.p. 90-96° C.

Provenance & Evidence