3-Pyridinecarboxaldehyde → N-[2-(4-Cyanophenoxy)ethyl]-N-{2-[7-(pyridin-3-ylmethyl)-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl]ethyl}methanesulfonamide

Participants

Reaction Steps

N-[2-(4-Cyanophenoxy)ethyl]-N-[2-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)ethyl]methanesulfonamide (79 mg, 0.2 mmol; see Example 3(ii) above) and pyridine-3-carbaldehyde (36 mg, 0.34 mmol) were dissolved in DCM (4 mL) and shaken for 1.5 h. Sodium triacetoxyborohydride (144 mg, 0.68 mmol) was added and the mixture was shaken overnight. The reaction was quenched with 1 M K2CO3 (2 mL) and was then phase-separated. The aqueous layer was washed with DCM (3×3 mL) and the organic layers were combined and evaporated. The residue was purified by chromatography on silica, which gave 66 mg (68%) of the title compound.

Provenance & Evidence