反应详情

温度

0 °C

Dissolve (R)-(+)-2-(tert-butoxycarbonylamino)-1-propanol (1.75 g, 10 mmol) and phenol (0.95 g, 10 mmol) in anhydrous THF (75 mL). Cool to 0° C., add triphenylphosphine (4.0 g, 15 mmol) and diisopropylazodicarboxylate dropwise and stir at ambient temperature for 18 h. Pour the mixture into water (300 mL), basify to pH 10 with 5N aqueous NaOH, and extract with ethyl ether (3×100 mL). Wash the organic phase with brine, dry over MgSO4, filter and concentrate. Purify by chromatography on silica gel eluting with hexane/EtOAc (9:1) to give the desired intermediate as an off-white solid (340 mg, 14%).

1. extractionbasify to pH 10 with 5N aqueous NaOH, and extract with ethyl ether (3×100 mL)
2. washWash the organic phase with brine
3. dry with materialdry over MgSO4
4. filtrationfilter
5. concentrationconcentrate
6. customPurify by chromatography on silica gel eluting with hexane/EtOAc (9:1)