Potassium Hydroxide → 1-Boc-1,2,5,6-tetrahydropyridine-3-carboxylic acid

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Reaction Steps

A solution of potassium hydroxide (44 g, 0.79 mol) in water (450 ml) was added to a solution of methyl 1-tert-butoxycarbonyl-1,2,5,6-tetrahydropyridine-3-carboxylate (34.9 g, 145 mmol) in methanol (450 ml). The mixture was refluxed for 3h and evaporated to dryness in vacuo. The residue acidified to pH 2.5 with hydrochloric acid (4M) and extracted with methylene chloride. The organic layer was dried over magnesium sulphate and evaporated to dryness in vacuo to give 1-tert-butoxycarbonyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid. (Yield: 28.4g, 86%)

Provenance & Evidence