Ethylbenzene → 3-(2-Nitro-1-pyridin-3-yl-ethyl)-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a cooled (−78° C.) solution of ethyl-1-BOC-3-piperidinecarboxylate (1.53 g, 10.20 mmol) in THF (15 ml) was added dropwise 2M LDA in heptane, THF, and ethylbenzene (5.34 ml, 10.69 mmol) and the resulting mixture was allowed to warm to −40° C. over 1 h and then cooled back to −78° C. A solution of 3-(2-nitroethenyl)pyridine (1.53 g, 10.20 mmol) in DMF (5 ml) was added dropwise and the reaction mixture was allowed to warm to RT over 1 h. The reaction was quenched with NH4Cl saturated aqueous solution (50 ml) and extracted with EtOAc (200 ml). The combined organic extracts were dried (MgSO4) and concentrated in vacuo. Purification of the crude product by chromatography on silica eluting with 0-10% MeOH in DCM afforded the title compounds as a yellow oil.

Provenance & Evidence