Sodium Hydroxide → (1-Isopropylpiperidin-4-yl)methanol

Participants

Reaction Steps

Under argon gas atmosphere, lithium aluminum hydride (3.29 g) is suspended in tetrahydrofuran (160 mL) and thereto is added ethyl 1-isopropylpiperidin-4-carboxylate (compound obtained in Reference Example 94(1), 5.00 g) under ice-cooling. The mixture is stirred at room temperature for 14 hours. To the reaction mixture is added successively water (3.3 mL), 2N sodium hydroxide solution (6.6 mL) and water (6.6 mL) under ice-cooling. The mixture is stirred at room temperature for 1 hour. After addition of magnesium sulfate, the reaction mixture is stirred for 10 minutes and filtered. The filtrate is concentrated in vacuo and the residue is purified by flash column chromatography on NH-silica gel (Solvent; n-hexane:ethyl acetate=1:1) to give (1-isopropylpiperidin-4-yl)methanol (3.75 g, yield; 99%) as a colorless oil. MS (APCI) m/z: 158 [M+H]+

Provenance & Evidence