反応 #2336527

反応方程式

oxalyl chloride

DMSO

triethylamine

1-(3-phenylpropionyl)-4-hydroxypiperidine

→

1-(3-phenylpropionyl)-4-ketopiperidine

収率 89.8%

溶媒

CH2Cl2

CH2Cl2

CH2Cl2

CH2Cl2

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   その他to come to room temperature
3. 3
   その他The mixture was quenched with saturated aqueous ammonium chloride solution
4. 4
   洗浄The organic phase was washed with water twice
5. 5
   乾燥with saturated brine, dried
6. 6
   その他evaporated under vacuum

実験手順

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.

出典