Acetic Acid → Tert-butyl 4-(3,3-dimethylcyclohexyl)-3-oxopiperazine-1-carboxylate

Participants

Reaction Steps

To a solution (0.19 M) of methyl N-(tert-butoxycarbonyl)-N-(2-oxoethyl)glycinate (prepared as described in Bioorg. Med. Chem. 2007, 15, 2092-2105) in MeOH were added 3,3-dimethylcyclohexanamine hydrochloride (1.5 eq), DIPEA (1.5 eq), NaBH3(CN) (1.5 eq) and AcOH (1.4 eq). After stirring for 2 hours at RT more NaBH3(CN) (1.5 eq) was added and reaction mixture was irradiated at MW for 1 hour at 125° C. MeOH was removed under reduced pressure and the residue purified by filtration on silica with elution of the desired intermediate with EtOAc. Evaporation of the organic solvent yielded tert-butyl 4-(3,3-dimethylcyclohexyl)-3-oxopiperazine-1-carboxylate. MS (ES) C17H30N2O3 requires: 310, found: 311 (M+H)+.

Provenance & Evidence