Reacción #72974

Ecuación de reacción

tert-butyl 4-oxopiperidine-1-carboxylate

sodium ethoxide

nitromethane

water

→

tert-butyl 4-hydroxy-4-(nitromethyl)piperidine-1-carboxylate

Disolventes

ethanol

ethanol

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe mixture was sonicated for 15 min
2. 2
   workup.STIRRINGstirred overnight
3. 3
   Otrosonicated again
4. 4
   OtroThe solid was isolated by filtration
5. 5
   Lavadowashed with water (300 mL)
6. 6
   Otrodried

Procedimiento

To a solution of tert-butyl 4-oxopiperidine-1-carboxylate (52.65 g, 264 mmol) in nitromethane (21 mL) and ethanol (8 mL) was added a solution of sodium ethoxide in ethanol (2.67 M, 5.0 mL, 13.4 mmol). The mixture was stirred at rt and more ethanol (30 mL) was added. The mixture was sonicated for 15 min, stirred overnight, then sonicated again. To the mixture was added water (400 mL). The solid was isolated by filtration, washed with water (300 mL), and dried to yield tert-butyl 4-hydroxy-4-(nitromethyl)piperidine-1-carboxylate as a white solid, 67.60 g (98%).

Fuente