tert-Butanol → HCID 69094616, compound

Participants

Reaction Conditions

Reaction Steps

Diphenylphosphoryl azide (1.2 eq) was added to a mixture of 3-methyl 1-(3-nitropyridin-4-yl)piperidine-3-carboxylic acid (1 eq) and anhydrous tBuOH (0.3 M), followed shortly by Et3N (2 eq). The reaction flask was fitted with an air-cooled reflux condenser and bubble vent, then heated in an 85° C. oil bath for 3 days. The crude mixture was diluted with EtOAc, washed with brine, then dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude residue was dissolved in CH2Cl2, loaded onto a SiO2 column, and purified by flash chromatography (10-20-40% EtOAc in hexanes) to give tert-butyl 3-methyl-1-(3-nitropyridin-4-yl)piperidin-3-ylcarbamate. LC/MS (m/z): 337.2 (MH+).

Provenance & Evidence