Sodium borohydride → tert-Butyl 4-(1-hydroxyethyl)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

tert-Butyl 4-acetylpiperidine-1-carboxylate from the previous step was dissolved in 50 ml methanol. NaBH4 (2.01 g, 53 mmol) was added in batches at 0° C. The resulting reaction mixture was stirred at 0° C. for 30 minutes. The volatiles were removed under vacuum. The residue was partitioned between 150 ml 10% KOH solution and 200 ml ether. The organic layers were washed with 100 ml brine, dried over sodium sulfate and concentrated to give 22.5 g colorless oil, which was azotropically dried by addition of 50 ml toluene and reconcentration under vacuum. This material was used for next step without further purification.

Provenance & Evidence