تفاعل #1620061

معادلة التفاعل

NaHCO3

Thionyl chloride

cyclohexanepropionic acid

pseudoephedrine

→

N-(1-Hydroxy-1-phenylprop-2-yl)-N-methyl-3-cyclohexylpropionamide

المذيبات

CH2Cl2

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was heated
2. 2
   درجة الحرارةat reflux for 60 min
3. 3
   أخرىthe solvent removed
4. 4
   workup.DISSOLUTIONThe residue was redissolved in THF (50 mL)
5. 5
   استخلاصwas then extracted with EtOAc
6. 6
   تجفيفThe organic phase was dried (MgSO4)
7. 7
   تركيزconcentrated
8. 8
   أخرىThe residue was chromatographed (silica gel; EtOAc/hexanes 1:1)
9. 9
   أخرىto afford an oil which
10. 10
    workup.WAITplaced in the refrigerator over night

الإجراء التجريبي

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)+.

المصدر