HCID 59682332, compound → HCID 58641432, compound

Participants

Reaction Conditions

Reaction Steps

Tert-butyl (2S)-2-phenyl-4-{[(trifluoromethyl)sulfonyl]oxy}-2,5-dihydro-1H-pyrrole-1-carboxylate (5-4, 100 mg, 0.254 mmol, 1 equiv) was added to a solution of dry THF (5 ml) containing copper iodide (5 mg, 0.025 mmol, 0.2 equiv) at −10° C. Cyclopropyl magnesium bromide (0.508 mL, 0.508 mmol, 2 equiv) was added drop wise and the resulting solution was stirred at −10° C. for 15 minutes. The reaction mixture was partitioned between aqueous ammonium chloride solution (15 mL) and ethyl acetate (3×10 mL). The combined organic layers were then dried over sodium sulfate, filtered, and concentrated to give tert-butyl (2S)-4-cyclopropyl-2-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate (32-1), which is converted to (2S)-4-cyclopropyl-N,N-dimethyl-2-phenyl-2,5-dihydro-1H-pyrrole-1-carboxamide (32-2) in the experimental mentioned above. 1H NMR (300 MHz, CDCl3) δ 7.22 (m, 5H), 5.82 (m, 1H), 5.35 (m, 1H), 4.43 (dd, J=14.5, 5.5 Hz, 1H), 4.00 (d, J=14.5 Hz, 1H), 2.82 (s, 6H), 1.40 (m, 1H), 0.76 (m, 2H), 0.54 (m, 2H). LRMS m/z (M+H) 257.2 found, 257.3 required.

Provenance & Evidence