Tetrahydrofuran → HCID 28345409, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the above ester (1.29 g, 4.79 mmol) in CH2Cl2 (20 mL) at 0° C. was added a solution of LiAlH4 in THF (1.0 M, 13.9 mL, 13.87 mmol) and the mixture was heated to reflux. After 1 h, the mixture was cooled back down to 0° C. and quenched with H2O (0.51 mL), 15% NaOH (0.51 mL), and H2O (1.53 mL). After stirring for 30 min, the reaction mixture was dried (MgSO4), filtered, and concentrated to afford [1-(toluene-4-sulfonyl)-piperidin-4-yl]-methanol as a clear oil (1.24 g, 100%). 1H NMR (CDCl3) δ 1.31-1.43 (m, 4H), 1.79 (d, 2H, J=12.0 Hz), 2.24 (t, 2H, J=12.0 Hz), 2.43 (s, 3H), 3.47 (d, 2H, J=6.0 Hz), 3.81 (d, 2H, J=12.0 Hz), 7.32 (d, 2H, J=6.0 Hz), 7.64 (d, 2H, J=6.0 Hz).

Provenance & Evidence