Water → 1-Benzyl-4-methylpiperidin-4-ol

Participants

Reaction Steps

Methyllithium (1.4 M in Et2O, 54.0 mL) was added to a solution of 1-benzyl-4-piperidone (5.00 mL, 27.0 mmol) in anhydrous ether at −78° C. under argon. Stirring was continued at −78° C. for 1.5 hours. Ether (200 mL) and water (40 mL) were added, and the two phases were separated. The aqueous solution was extracted with Et2O (3×50 mL). The combined organic solutions were dried over magnesium sulfate and concentrated. The residue was chromatographed (EtOAc to EtOAc-MeOH 9/1), giving 4.81 g (87%) of the desired product as a colorless oil: 1H NMR δ 1.21 (s, 3 H), 1.56 (dt, J=13, 3 Hz, 2 H), 1.65 (td, J=10, 4 Hz, 2 H), 2.35 (td, J=10, 3 Hz, 2 H), 2.53 (m, 2 H), 7.24 (m, 1 H), 7.29 (m, 4 H); 13C NMR δ 30.44, 39.37, 50.39, 63.80, 68.50, 127.56, 128.80, 129.80, 139.17.

Provenance & Evidence