1-Benzyl-4-piperidone → HCID 57979767, compound

Participants

Reaction Steps

Following the procedure of N. I. Carruthers et al. (J. Med. Chem. 2005, 48, 1857-1872), to a −78° C. solution of 2-bromo-3-methylpyridine (10.0 g, 7.1 mL, 57.1 mmol) in THF (150 mL) was added drop wise a solution of n-BuLi (2.5 M in hexanes, 25.1 mL, 62.8 mmol) over 10 min. After 1.5 h a solution of N-benzyl-4-piperidone (10.8 g, 57.1 mmol) in THF (20 mL) was added drop wise over 15 min and the mixture was allowed to slowly warm to room temperature overnight. After 18 h sat. NH4Cl solution (40 mL) was added and the mixture was concentrated. The resulting residue was diluted with 1N NaHCO3 (100 ml) and extracted with EtOAc. The combined organic phase washed with brine, dried (MgSO4), and concentrated. Flash chromatography afforded the alcohol (8.1 g), an orange viscous oil, in 50% yield.

Provenance & Evidence