Reacción #159983

Ecuación de reacción

3-(4-Methyl-benzoyl)-4-oxo-piperidine-1-carboxylic acid tert-butyl ester

pyrrolidine-1-carboxamidine trifluoroacetate

sodium tert-butoxide

→

title compound

Rendimiento 36.7%

2-Pyrrolidin-1-yl-4-p-tolyl-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine-6-carboxylic acid tert-butyl ester

Rendimiento 36.7%

Disolventes

t-BuOH

H2O

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was heated
2. 2
   Temperaturaat reflux for 2 h
3. 3
   Extracciónextracted with CH2Cl2 (2×)
4. 4
   OtroThe combined organic extracts were dried
5. 5
   Concentraciónconcentrated
6. 6
   OtroThe residue was purified by FCC

Procedimiento

To a mixture of 3-(4-Methyl-benzoyl)-4-oxo-piperidine-1-carboxylic acid tert-butyl ester (0.24 g, 0.74 mmol) and pyrrolidine-1-carboxamidine trifluoroacetate (0.14 g, 0.58 mmol) in t-BuOH (7.5 mL) was added sodium tert-butoxide (0.10 g, 1.1 mmol). The mixture was heated at reflux for 2 h, then cooled to rt, diluted with H2O and extracted with CH2Cl2 (2×). The combined organic extracts were dried and concentrated. The residue was purified by FCC to give the title compound (0.084 g, 29%) as a clear oil. MS (ESI): mass calcd. for C23H30N4O2, 394.5; m/z found, 395.5 [M+H]+.

Fuente