Reacción #69495

Ecuación de reacción

(R)-tert-Butyl 2-(6-(methoxycarbonyl)-2-(2-methylmorpholino)-4-oxo-4H-chromen-8-yl)-1H-pyrrole-1-carboxylate

→

tert-butyl 2-(6-(methoxycarbonyl)-2-((R)-2-methylmorpholino)-4-oxo-4H-chromen-8-yl)pyrrolidine-1-carboxylate

Rendimiento 59.0%

Disolventes

MeOH

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONMore catalyst was added
2. 2
   workup.WAITfollowed by the same amount after 1 h
3. 3
   workup.WAITafter another 2 h
4. 4
   FiltraciónThe catalyst was filtered through celite
5. 5
   Lavadowashed with MeOH/DCM
6. 6
   Otrothe solvent evaporated
7. 7
   OtroThe crude product was purified by flash chromatography on silica gel eluting with 10 to 15% MeOH in EtAc
8. 8
   OtroThe solvent was evaporated to dryness

Procedimiento

(R)-tert-Butyl 2-(6-(methoxycarbonyl)-2-(2-methylmorpholino)-4-oxo-4H-chromen-8-yl)-1H-pyrrole-1-carboxylate (2 g, 4.27 mmol) and 5% Rhodium on Alumina (50% wet) (0.4 g, 0.09 mmol) in MeOH (50 mL) were stirred under an atmosphere of hydrogen at 5 bar and 65° C. for 2 h. More catalyst was added and stirring continued overnight. 2 g of 5% Rh/C was then added followed by the same amount after 1 h then after another 2 h. The catalyst was filtered through celite and washed with MeOH/DCM and the solvent evaporated. The crude product was purified by flash chromatography on silica gel eluting with 10 to 15% MeOH in EtAc. The solvent was evaporated to dryness to afford tert-butyl 2-(6-(methoxycarbonyl)-2-((R)-2-methylmorpholino)-4-oxo-4H-chromen-8-yl)pyrrolidine-1-carboxylate (1.18 g, 59%) as a white solid. Mass Spectrum: m/z [M+H]+=473.

Fuente