4-Toluenesulfonyl chloride → HCID 70976328, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (6S,7aS)-6-Amino-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-one (example 20, step d) (80 mg, 0.266 mmol), 4-Methyl-benzenesulfonyl chloride (101 mg, 0.53 mmol) and NEt3 (100 mg, 0.99 mmol) in DCM (10 mL) was stirred at 10° C. overnight. The mixture was washed with water (5 mL×3), dried with anhydrous sodium sulfate and then purified with silica gel column chromatography (eluting with DCM/MeOH=150:1) to 58 mg (46%) of the title compound as a white solid. 1H NMR (300 MHz, CDCl3): δ 7.72 (d, 2H, J=9 Hz), 7.31 (d, 2H, J=9 Hz), 7.24 (d, 2H, J=6 Hz), 7.04 (d, 2H, J=9 Hz), 6.00 (d, 1H, J=9 Hz), 4.07-4.00 (m, 1H) 3.76-3.74 (m, 2H), 3.49-3.36 (m, 2H), 3.22-3.19 (m, 1H), 2.47 (s, 3H), 2.23-2.15 (m, 1H), 1.55-1.44 (m, 1H); LC-MS: 456.1 [M+1]+.

Provenance & Evidence