Hydrochloric Acid → Tert-butyl 3-(hydroxymethyl)-4-methylpiperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A flask containing (+/−)-4-methyl-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (5.96 g, 21.94 mmol) in dry tetrahydrofuran (40 mL) was cooled to 0° C. (ice bath) under argon atmosphere. A solution of lithium aluminum hydride (19.4 mL, 1M in tetrahydrofuran) was added via slow drop-wise addition. The cooled mixture was stirred for 2 hours. A solution of 1 M hydrochloric acid (23 mL) was added via slow drop-wise addition. After 10 minutes powdered magnesium sulfate was added followed by the addition of ethyl acetate (80 mL). The mixture was filtered through a plug of celite, rinsing well with ethyl acetate. The filtrate was stripped providing 5.08 g of (+/−)-3-hydroxymethyl-4-methyl-piperidine-1-carboxylic acid tert-butyl ester as a clear semi-mobile oil. MS (M+Na)+=252.

Provenance & Evidence