Aluminium lithium hydride → HCID 86682893, compound

Participants

Reaction Steps

A solution of (S)-2-(3,3-dimethyl-2,5-dioxopyrrolidin-1-yl)propyl acetate (6.15 g, 27.1 mmol) in anhydrous diethyl ether (20 mL) was added to a suspension of LiAlH4 (3.0 g, 79 mmol) in anhydrous diethyl ether (250 mL) at room temperature under nitrogen atmosphere. After stirring at room temperature overnight, the reaction mixture was quenched with H2O (3 mL). The resulting suspension was filtered, and the filter cake was washed with ethyl acetate (50 mL). The combined filtrate was concentrated under reduced pressure, and the residue was purified on a silica gel column (eluting with DCM/MeOH=20/1) to give (S)-2-(3,3-dimethylpyrrolidin-1-yl)propan-1-ol (2.37 g, 59%). 1H NMR (CDCl3): δ 3.53 (dd, 1H), 3.27 (dd, 1H), 2.70 (m, 3H), 2.37 (s, 2H), 1.55 (m, 2H), 1.07 (s, 3H), 1.06 (s, 3H), 0.94 (d, 3H); LCMS: 158 (M+H)+.

Provenance & Evidence