Sodium Chloride → 3-Pyridin-3-ylcyclohexanamine

Participants

Reaction Conditions

Reaction Steps

Hydroxylamine hydrochloride (67.7 mg, 0.975 mmol) was added to a stirred mixture of 8c (122 mg, 0.696 mmol) and potassium carbonate (96.0 mg, 0.696 mmol) in MeOH (3.00 mL) and water (600 μl). After the reaction was deemed to be complete, the reaction mixture was partially concentrated in vacuo and partitioned between EtOAc and brine. The layers were separated, and the aq. layer was extracted with EtOAc. The combined organics were dried (Na2SO4), filtered and concentrated in vacuo to afford a crude residue (m/z (ES) 191 (MH)+), which was dissolved in THF (3.50 mL) and cooled to 0° C. Lithium aluminum hydride (106 mg, 2.78 mmol) was added in several portions, and after the reaction was deemed to be complete, 1N NaOH was added. The resulting mixture was saturated with NaCl(s) and extracted with EtOAc. The combined organics were dried (Na2SO4), filtered and concentrated in vacuo to afford the title compound, 8d. m/z (ES) 177 (MH)+

Provenance & Evidence