1-((((1-(2-(Benzyloxy)-2-oxoethyl)cyclohexyl)methyl)carbamoyl)oxy)ethyl Isobutyrate → Gabapentin Enacarbil

Participants

Reaction Steps

Compound (10) (113 g) was dissolved in ethyl acetate (700 mL) and 10 g of 10% Pd-C was added. The reaction mixture was subjected to 50 psi of hydrogen gas in a Parr reactor for 40 min. Filtration through a sintered glass funnel and a hydrophobic membrane filtration cartridge (Millipore Opticap) removed the catalyst. The supernatant was concentrated to afford the product (11) as a white, crystalline solid (78 g, quantitative yield). Crystals formed in the freezer, then at room temperature over several days. 1H NMR (CDCl3, 400 MHz): 1.15 (d, 6H), 1.40–1.55 (m, 10H), 1.45 (d, 3H), 2.32 (s, 2H), 2.49–2.56 (m, 1H), 3.23 (d, 2H), 5.41 (t, 1H), 6.75 (q, 1H). MS(ESI) m/z 330.29 (M+H+).

Provenance & Evidence