Reacción #89699

Ecuación de reacción

NH4Cl

tert-butyl 3-oxopyrrolidine-1-carboxylate

phenylmagnesium bromide

→

desired product

Rendimiento 49.2%

tert-butyl 3-hydroxy-3-phenylpyrrolidine-1-carboxylate

Rendimiento 49.2%

Disolventes

ether

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction was heated
2. 2
   Temperaturato reflux for 15 min
3. 3
   Extracciónextracted with ether (3×)
4. 4
   SecadoThe combined organic layers were dried over Na2SO4
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   OtroThe crude residue was purified by flash column chromatography

Procedimiento

To a solution of tert-butyl 3-oxopyrrolidine-1-carboxylate (1 g, 5.40 mmol) in ether (20 ml) was added dropwise phenylmagnesium bromide (10.3 mL, 3.0 M in ether, 6.21 mmol) at rt under nitrogen. The reaction was heated to reflux for 15 min, then cooled to rt, poured into sat. NH4Cl, extracted with ether (3×). The combined organic layers were dried over Na2SO4, concentrated in vacuo. The crude residue was purified by flash column chromatography to yield the desired product (700 mg, 49.24%). LCMS (M+H) 264.160.

Fuente