Reacción #2336527

Ecuación de reacción

oxalyl chloride

DMSO

triethylamine

1-(3-phenylpropionyl)-4-hydroxypiperidine

→

1-(3-phenylpropionyl)-4-ketopiperidine

Rendimiento 89.8%

Disolventes

CH2Cl2

CH2Cl2

CH2Cl2

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   Otroto come to room temperature
3. 3
   OtroThe mixture was quenched with saturated aqueous ammonium chloride solution
4. 4
   LavadoThe organic phase was washed with water twice
5. 5
   Secadowith saturated brine, dried
6. 6
   Otroevaporated under vacuum

Procedimiento

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.

Fuente