Hydrochloric Acid → 1-(1,1-Dimethylethyl) 3,6-dihydro-1,3(2H)-pyridinedicarboxylate

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Reaction Steps

A solution of 1-tert-butoxycarbonyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid (6.5 g, 28.6 mmol) in dry tetrahydrofuran (150 ml) was added dropwise to a mixture of 2.5 M butyllithium in hexane (25 ml, 62.5 mmol) and diisopropylamine (6.37 g, 63.1 mmol) in dry tetrahydrofuran (150 ml) at <-65° C. Stirring was continued for 20 min. -10°C. The mixture was poured into 1 M aqueous HCl (100 ml) while cooling with ice. The resulting mixture was extracted several times with ethyl acetate (a total of 500 ml). The organic layer was dried over magnesium sulphate and evaporated to dryness in vacuo to give 1-tert-butoxycarbonyl-1,2,3,6-tetrahydropyridine-3-carboxylic acid (Yield: 6.3 g, 97%).

Provenance & Evidence