6-(2-tert-Butoxycarbonyl-vinyl)-pyridine-2-carboxylic acid methyl ester → 6-(2-tert-Butoxycarbonyl-ethyl)-piperidine-2-carboxylic acid methyl ester

Participants

Reaction Steps

Compound 2 (1.0 g) is dissolved in glacial acetic acid (10 ml) and PtO2 (100 mg) is added. Hydrogenation is carried out in Parr shaker at 55 psi for 3 days. The catalyst is removed by filtration through Celite, and the solvent is evaporated to give the desired product as a yellow oil. 1H NMR (CD3OD) δ 3.73 (s, 3H), 3.40-3.33 (m, 1H), 2.61-2.52 (m, 1H), 2.34-2.29 (m, 2H), 2.03-1.99 (m, 1H), 1.93-1.88 (m, 1H), 1.76-1.68 (m, 3H), 1.50-1.33 (m, 11H), 1.11-1.02 (m, 1H).

Provenance & Evidence