Pyridine → HCID 86696303, compound

Participants

Reaction Steps

In a manner similar to the method described in Example 3, 1-chloroethyl chloroformate (Oakwood, 1.32 g, 1.0 mL, 9.27 mmol) was reacted with 4-aminotetrahydropyrane (Oakwood, 899 mg, 0.92 mL, 8.62 mmol) and pyridine (782 mg, 0.8 mL, 9.89 mmol) in methylene chloride (20 mL) at −78° C. for 3 h to give 1-chloroethyl tetrahydro-2H-pyran-4-ylcarbamate compound with pyridine hydrochloride (1:1). A portion of this material (520 mg, 1.61 mmol) in dimethylformamide (5 mL) was then reacted with chiral 4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-3-methoxybenzoic acid (151.4 mg, 0.246 mmol) and cesium carbonate (599.5 mg, 1.84 mmol) in dimethylformamide (4.00 mL) at room temperature for 17 h to give 1-(tetrahydro-2H-pyran-4-ylcarbamoyloxy)ethyl 4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-3-methoxybenzoate as a white solid (145.7 mg, 75% yield). MS (ES+) m/z calcd. for C39H42Cl2F2N4O7: [(M+H)+]: 787, found: 787

Provenance & Evidence