Lithium hydroxide, monohydrate → 1-(tert-butoxycarbonyl)-4-(hydroxymethyl)piperidine-4-carboxylic acid

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Reaction Conditions

Reaction Steps

Lithium hydroxide monohydrate (6.95 g, 165.6 mmol) was added to solution of N-(tert-butoxycarbonyl)-4-(hydroxymethyl)piperidine-4-carboxylic acid ethyl ester (9.52 g, 33.1 mmol) in 2:1 methanol/water (100 mL). The mixture was heated to reflux for 30 minutes, the methanol removed in vacuo by concentration using a bath temperature no higher than 45° C. The aqueous layer was cooled to 0° C., acidified to pH 3.0 using 6M aqueous hydrochloric acid, and extracted with ethyl acetate (4×75 mL). The combined organic layers were dried over magnesium sultate, and concentrated in vacuo, and recrystallized from dichloromethane/hexanes to afford N-(tert-butoxycarbonyl)-4-(hydroxymethyl)piperidine-4-carboxylic acid (8.59 g, 100%).

Provenance & Evidence