(1-Cyanocyclohexyl)acetic acid → Gabapentin

Reaction equation

[C:1]([C:3]1([CH2:9][C:10]([OH:12])=[O:11])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)#[N:2].[H][H]>CO.[C].[Rh]>[CH2:6]1[CH2:5][CH2:4][C:3]([CH2:1][NH2:2])([CH2:9][C:10]([OH:12])=[O:11])[CH2:8][CH2:7]1

Participants

Procedure

A solution of 3 g (1-cyanocyclohexyl)-acetic acid in 10.5 mL methanol is hydrogenated at 10 bar hydrogen pressure and 30° C. in the presence of rhodium-carbon (5%) over a period of five hours. The reaction mixture is filtered and the filtrate evaporated on a rotary evaporator at 30° C. The crystalline residue is stirred with isopropanol and the crystallizate is filtered off with suction and dried to constant weight in a vacuum drying cabinet at 30° C. 2.0 g of the title compound are obtained (65.2% of theory); m.p. 152° C.