反应详情

Thionyl chloride (3.5 mL, 48 mmol) was added to a solution of cyclohexanepropionic acid (5.5 mL, 32 mmol) in CH2Cl2 (60 mL). The mixture was heated at reflux for 60 min and then allowed to cool to ambient temperature and the solvent removed. The residue was redissolved in THF (50 mL) and (1R,2R) pseudoephedrine (4.8 g, 29 mmol) in THF (60 mL) was added to the reaction mixture at 0° C. After stirring for 30 min, a solution of saturated NaHCO3 was added to the mixture which was then extracted with EtOAc. The organic phase was dried (MgSO4) and concentrated. The residue was chromatographed (silica gel; EtOAc/hexanes 1:1) to afford an oil which solidified when placed in the refrigerator over night (8.2 g, 94%). MS (CI/NH3) m/z: 304 (M+H)+.

1. temperatureThe mixture was heated
2. temperatureat reflux for 60 min
3. customthe solvent removed
4. dissolutionThe residue was redissolved in THF (50 mL)
5. extractionwas then extracted with EtOAc
6. dry with materialThe organic phase was dried (MgSO4)
7. concentrationconcentrated
8. customThe residue was chromatographed (silica gel; EtOAc/hexanes 1:1)
9. customto afford an oil which
10. waitplaced in the refrigerator over night