Phosgene → HCID 67095081, compound

Participants

Reaction Steps

In a manner similar to the method described in Example 4, rac-(2S,3S,4S)-2-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-4-(2,2-dimethyl-propyl)-pyrrolidine-3-carbonitrile (42.3 mg, 0.10 mmol) was reacted with phosgene solution (Aldrich, 20% in toluene, 0.12 mL, 0.12 mmol), in the presence of triethylamine (TEA, 30.0 mg, 0.30 mmol) in CH2Cl2 (2 mL) followed by reacting with 1-ethyl-piperazine (17.2 mg, 0.15 mmol) at rt for 30 min to give rac-(2S,3S,4S)-2-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-4-(2,2-dimethyl-propyl)-1-(4-ethyl-piperazine-1-carbonyl)-pyrrolidine-3-carbonitrile (20.6 mg, 30.4%, as TFA salt) as a white amorphous. HRMS (ES+) m/z Calcd for C29H34Cl2F2N4O+H [(M+H)+]: 563.2151, found: 563.2151.

Provenance & Evidence