Phenylacetonitrile → Tert-butyl 4-[cyano(phenyl)methyl]-4-hydroxypiperidine-1-carboxylate

Participants

Reaction Steps

Benzyl cyanide (2.96 ml, 25.6 mmol) in THF (125 ml) was cooled to −78° C. nBuLi (16.17 ml, 25.9 mmol) was added dropwise over 20 min via syringe pump, and the reaction stirred for 30 min. 1-BOC-4-piperidone (5.10 g, 25.6 mmol) in THF (20 ml) was added over 20 min via syringe pump and the reaction stirred for 2.5 hours. While still cold, the reaction was quenched with satd. NH4Cl and allowed to warm overnight. The mixture was partitioned between CH2Cl2 and satd. NH4Cl, the aqueous portion extracted 3×CH2Cl2, and the organic portion dried (Na2SO4) then concentrated in vacuo. The resulting material was carried on without further purification.

Provenance & Evidence