Phosgene → 4-{[(3R,4S)-3-({(1R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethyl}oxy)-4-phenylpyrrolidin-1-yl]carbonyl}-1,3-oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 15 mg (0.03 mmol) 2-amino-3-[(3R,4S)-3-({(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}oxy)-4-phenylpyrrolidin-1-yl]-3-oxopropan-1-ol (Example 5) in 3 mL methylene chloride was added 0.011 mL (0.08 mmol) triethylamine. The resulting mixture was cooled to 0° C. and 0.015 mL (0.03 mmol) of a 2M solution of phosgene in toluene was added by syringe. The reaction mixture was stirred at RT for 8 hr and the volatiles were removed under vacuum. The dark yellow residue was purified by prep TLC eluting with methylene chloride/methanol (95/5) to afford the title compound. 1H-NMR (CDCl3) rotamers: δ: 1.43 (d, 3H, 6.5 Hz), 3.30-4.13 (m, 7H), 4.40-4.70 (m, 3H), 7.00-7.10 (m, 2H), 7.20-7.30 (m, 3H), 7.55 (s, 2H), 7.60 (s, 1H), 7.75, 7.77 (2s, 1H)ppm. MS: 517.0 (MH+) observed.

Provenance & Evidence