반응 #2336527

반응 방정식

oxalyl chloride

DMSO

triethylamine

1-(3-phenylpropionyl)-4-hydroxypiperidine

→

1-(3-phenylpropionyl)-4-ketopiperidine

수율 89.8%

용매

CH2Cl2

CH2Cl2

CH2Cl2

CH2Cl2

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   기타to come to room temperature
3. 3
   기타The mixture was quenched with saturated aqueous ammonium chloride solution
4. 4
   세척The organic phase was washed with water twice
5. 5
   건조with saturated brine, dried
6. 6
   기타evaporated under vacuum

실험 절차

To 1.68 mL of oxalyl chloride (19.2 mmol) in 35 mL of CH2Cl2 at −78° C. was added 2.73 mL (38.5 mmol) of dry DMSO in 5 mL of CH2Cl2. After the addition, 3.6 g (15.4 mmol) of 1-(3-phenylpropionyl)-4-hydroxypiperidine 134 in 5 mL of CH2Cl2 was added, and the mixture was stirred for 5 min in the cold. 10.73 mL (77 mmol) of triethylamine in 5 mL of CH2Cl2 was added, and the mixture was allowed to come to room temperature. The mixture was quenched with saturated aqueous ammonium chloride solution. The organic phase was washed with water twice, with saturated brine, dried, and evaporated under vacuum to give 3.2 g (89) of 1-(3-phenylpropionyl)-4-ketopiperidine (135). GC/MS showed 100% purity with a molecular ion of 231.

출처