Reacción #2449955

Ecuación de reacción

1-(tert-butoxycarbonyl)-3-piperidinecarboxylic acid

2-phenylpiperidine

DIPEA

EDCI

HOBT

→

title compound

Rendimiento 31.1%

3-(2-Phenyl-piperidine-1-carbonyl)-piperidine-1-carboxylic acid tert.-butyl ester

Rendimiento 31.1%

Disolventes

brine

DMF DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe mixture was stirred for 6 h at room temperature
2. 2
   Extracciónextracted with ethyl acetate (2×40 mL)
3. 3
   SecadoThe combined organic layers were dried over sodium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Otroevaporated at reduced pressure
6. 6
   Otroto obtain the crude product, which
7. 7
   Otrowas further purified by column chromatography on silica eluting with 30-35% ethyl acetate in hexane

Procedimiento

To a solution of 2 g of 1-(tert-butoxycarbonyl)-3-piperidinecarboxylic acid (commercially available) (8.72 mmol) in 15 mL of DMF:DCM (3:1) was added 1.39 g 2-phenylpiperidine (commercially available) (8.72 mmol) and 3.04 mL DIPEA (17.4 mmol). The mixture was stirred at room temperature for 10 minutes. 2.5 g EDCI (13.1 mmol) and 2.04 g HOBT (13.1 mmol) was added. The mixture was stirred for 6 h at room temperature, diluted with brine (50 mL) and extracted with ethyl acetate (2×40 mL). The combined organic layers were dried over sodium sulfate, filtered and evaporated at reduced pressure to obtain the crude product, which was further purified by column chromatography on silica eluting with 30-35% ethyl acetate in hexane to yield 1 g (31%) of the title compound. (MH+) 372.18.

Fuente