(2-Bromoethyl)cyclohexane → HCID 67189860, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of [6-(hydroxymethyl)pyridin-2-yl]carbamate (200 mg, 1.07 mmol) in DMF, cooled to 0° C. with a brine/ice bath, was added potassium tert-butoxide (126 mg, 1.07 mmol). The mixture was stirred 5 minutes at 0° C. then 1-bromo-2cyclohexylethane (205 mg, 1.07 mmol) was added. After stirring at room temperature for 4 h, the reaction mixture was diluted with ethyl acetate and water. The organic layer was washed with water, dried over MgSO4 and concentrated in vacuo. Purification on silica gel afforded tert-butyl (2-cyclohexylethyl)[6-(hydroxymethyl)pyridin-2-yl]carbamate as a yellow oil [240 mg, yield 64%; HPLC/MS: m/z=335 (M+H); logP(HCOOH)=4.49]

Provenance & Evidence