Reacción #72967

Ecuación de reacción

ethyl 4-hydroxy-4-(nitromethyl)piperidine-1-carboxylate

→

ethyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe mixture was filtered through CELITE
2. 2
   Filtraciónfilter agent
3. 3
   Concentraciónthe filtrate was concentrated
4. 4
   Otrothe crude material was subjected to the reaction conditions again with fresh 20% palladium hydroxide on carbon (0.50 g) for another 24 h
5. 5
   FiltraciónThe mixture was filtered through CELITE
6. 6
   Filtraciónfilter agent
7. 7
   Concentraciónthe filtrate was concentrated

Procedimiento

A mixture of ethyl 4-hydroxy-4-(nitromethyl)piperidine-1-carboxylate (5.2 g, 22.4 mmol) and 20% palladium hydroxide on carbon (0.50 g) in ethanol (190 mL) was hydrogenated at 35 psi (2.4×105 Pa) on a Parr apparatus for 5 h. The mixture was filtered through CELITE filter agent and the filtrate was concentrated. By 1H NMR analysis, the reaction was incomplete and the crude material was subjected to the reaction conditions again with fresh 20% palladium hydroxide on carbon (0.50 g) for another 24 h. The mixture was filtered through CELITE filter agent and the filtrate was concentrated to provide ethyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate, which was concentrated from chloroform to remove residual ethanol before using in the next reaction.

Fuente