Reacción #1520092

Ecuación de reacción

Ethyl acetate

Sodium hydride

(2S, 6R)-2,6-Dimethyl-3-oxo-piperazine-1-carboxylic acid benzyl ester

7-bromomethyl-4-chloro-quinoline

→

(2S,6R)-4-(4-chloro-quinolin-7-ylmethyl)-2,6-dimethyl-3-oxo-piperazine-1-carboxylic acid benzyl ester

Rendimiento 83.0%

Disolventes

DMF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITthe reaction is left
2. 2
   workup.ADDITIONis added
3. 3
   Otrothe reaction is quenched with 3 mL of H2O
4. 4
   OtroThe two layers are separated
5. 5
   Extracciónto extract
6. 6
   Secadodried over magnesium sulfate
7. 7
   FiltraciónThe residue after filtration and concentration
8. 8
   Otrois chromatographed on silica gel (60% EtOAc/Hexane)

Procedimiento

(2S, 6R)-2,6-Dimethyl-3-oxo-piperazine-1-carboxylic acid benzyl ester (750 mg, 2.86 mmol) is dissolved in 20 mL of THF and 2 mL of DMF. Sodium hydride (60%, 142.6 mg, 6.20 mmol) is added at 0° C., and the reaction is left to stir at room temperature for thirty minutes at which time the 7-bromomethyl-4-chloro-quinoline (952 mg, 3.72 mmol) is added. The reaction is complete after stirring for four hours. Ethyl acetate (200 mL) is added to the mixture, and the reaction is quenched with 3 mL of H2O. The two layers are separated, and ethyl acetate (2×30 mL) is used to extract and dried over magnesium sulfate. The residue after filtration and concentration is chromatographed on silica gel (60% EtOAc/Hexane) to give (2S,6R)-4-(4-chloro-quinolin-7-ylmethyl)-2,6-dimethyl-3-oxo-piperazine-1-carboxylic acid benzyl ester (1.04 g, 83%).

Fuente