Реакция #2336527

Уравнение реакции

oxalyl chloride

DMSO

triethylamine

1-(3-phenylpropionyl)-4-hydroxypiperidine

→

1-(3-phenylpropionyl)-4-ketopiperidine

Выход 89.8%

Растворители

CH2Cl2

CH2Cl2

CH2Cl2

CH2Cl2

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added
2. 2
   Другоеto come to room temperature
3. 3
   ДругоеThe mixture was quenched with saturated aqueous ammonium chloride solution
4. 4
   ПромывкаThe organic phase was washed with water twice
5. 5
   Сушкаwith saturated brine, dried
6. 6
   Другоеevaporated under vacuum

Методика

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.

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