Acetic Acid → HCID 67315281, compound

Participants

Reaction Conditions

Reaction Steps

To an ice cold solution of 1-benzyl-3,3-dimethyl-piperidin-4-one (0.5 g, 2 mmol) (J. Med. Chem. Lett. 2003, 13, 1627) in CH2Cl2 (10 ml) was added methyl 4-aminobutyrate hydrochloride (0.7 g, 5 mmol), acetic acid (0.4 ml, 7 mmol), triethylamine (0.5 ml, 5 mmol) and sodium triacetoxyborohydride (0.5 g, 3 mmol). The mixture was allowed to reach room temperature and was stirred for 16 h after which time it was washed with saturated sodium hydrogen carbonate solution, dried (Na2SO4) and concentrated. The residue (0.6 g, 2 mmol) was then redissolved in MeOH (10 ml), potassium carbonate (0.3 g, 2 mmol) added and the mixture heated to 70° C. for 2 h. The mixture was then filtered, the methanol evaporated and the residue redissolved in DMF (10 ml) and reacted with EDCl (0.4 g, 2 mmol) at 60° C. for 2 h after which time the DMF was evaporated, the residue taken up in CH2Cl2, washed with saturated sodium hydrogen carbonate solution, dried (Na2SO4) and concentrated. Flash column chromatography (EtOAc:n-heptane 2:1) afforded the title compound (0.4 g, 85%) as yellow oil. MS: 287.4 (MH+).

Provenance & Evidence