Aluminium lithium hydride → (1-Benzylpyrrolidine-2,5-diyl)dimethanol

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Reaction Steps

A solution of 96.4 grams of 1-benzyl-pyrrolidine-2,5-dicarboxylic acid, 2-ethyl ester, 5-methyl ester in 380 ml of anhydrous tetrahydrofuran is dripped rapidly into a solution of lithium aluminum hydride (437 mmol) in tetrahydrofuran (1.4 liter) at 0° C. After complete addition, the mixture is stirred for 3 hours at ambient temperature and then carefully quenched with 57.8 ml of water followed by 38.6 ml of 10% sodium hydroxide. The mixture is stirred overnight, filtered through Celite, the Celite washed with CH2Cl2 and the combined filtrate evaporated to provide 67.11 grams of crude (1-benzyl-5-hydroxymethyl-pyrrolidine-2-yl)-methanol.

Provenance & Evidence