反应详情

To a solution of 38 mg (0.094 mmol) (3R,4S)-3-({(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}oxy)-4-phenylpyrrolidine (Example 1. Step E) in 7.5 mL methylene chloride was added 12.7 mg (0.094 mmol) HOBT, 34.7 mg (0.14 mmol) 3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-4-carboxylic acid, 0.04 mL (0.28 mmol) triethylamine and 54 mg (0.28 mmol) EDC. The resulting mixture was stirred at RT for 16 hr. The reaction mixture was partitioned between 5 mL brine and extracted with EtOAc (3×5 mL). The combined organic layers were dried over sodium sulfate, filtered and the solvent removed under vacuum. The yellow oil was purified by prep TLC eluting with methylene chloride/methanol (95/5) to give the title compound. 1H-NMR (CDCl3) rotamers: δ: 1.4-1.8 (m, 18H), 3.20-3.70 (m, 2H), 3.88-4.3 (m, 3H), 4.43-4.70 (m, 1H), 6.97-7.10 (m, 2H), 7.20-7.35 (m, 3H), 7.53. 7.55, 7.62 (3s, 2H), 7.75, 7.78 (2s, 1H)ppm. MS: 631.3 (MH+) observed.

1. customThe reaction mixture was partitioned between 5 mL brine
2. extractionextracted with EtOAc (3×5 mL)
3. dry with materialThe combined organic layers were dried over sodium sulfate
4. filtrationfiltered
5. customthe solvent removed under vacuum
6. customThe yellow oil was purified by prep TLC
7. washeluting with methylene chloride/methanol (95/5)