Methanol → Ethyl 4-hydroxypiperidine-1-carboxylate

Participants

Reaction Steps

To a suspension of 68.5 parts of ethyl 4-oxo-1-piperidinecarboxylate in 240 parts of methanol were added portionwise 3.8 parts of sodium borohydride at a temperature between 20°-30° C. (the reaction mixture was cooled if necessary in a water bath). After the addition was complete, the whole was stirred for 30 minutes. The reaction mixture was then poured into a mixture of 53.5 parts of ammonium chloride and 400 parts of water. The methanol was evaporated. The product was extracted with trichloromethane. The extract was dried and evaporated. The oily residue was distilled in vacuo, yielding 60 parts of oily ethyl 4-hydroxy-1-piperidinecarboxylate; bp. 140° C. at 1.4 mm. pressure; nD20 : 1.4796; d2020 : 1.1166 (3).

Provenance & Evidence