Sodium Hydroxide → 1-Methyl-4-piperidinemethanol

Participants

Reaction Conditions

Reaction Steps

To a suspension of lithium aluminum hydride (0.88 g, 23 mmol) in tetrahydrofuran (50 mL) was added dropwise a solution of Example 59 (1.03 g, 6 mmol) in tetrahydrofuran (10 mL) and the mixture was heated to reflux for about 2 hours. The mixture was cooled to about 0° C. and saturated aqueous sodium hydroxide (3.5 mL) was added dropwise. After stirring for about 10 minutes at room temperature, the mixture was filtered, the filter cake was washed with tetrahydrofuran and the combined filtrates were dried (Na2SO4), filtered and concentrated under vacuum to provide the desired product. 1H NMR (500 MHz, CDCl3): δ 1.10 (m, 1H), 1.60-2.00 (m, 4H), 2.10 (m, 2H), 2.28 (s, 3H), 2.65 (m, 1H), 2.82 (m, 1H), 3.57 (dd, J=8, 14 Hz, 1H), 3.63 (dd, J=8, 14 Hz, 1H), 3.70 (m, 1H).

Provenance & Evidence