Acetic Acid → HCID 59828914, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, add sodium cyanoborohydride (3.53 g, 56 mmol) to a solution of 3-aminomethyl-6-chloro-pyridine (2 g, 14 mmol), cyclohexanone (1.38 g, 14 mmol) and acetic acid (168 mg, 0.2 mmol) in methanol (20 mL) at 0° C. Warm the mixture to room temperature and stir overnight. Add water (100 mL) and saturated aqueous K2CO3. Extract three times with DCM and wash the combined organic extracts with water and brine. Dry over Na2SO4, filter, and concentrate in vacuo. Purify by chromatography on silica gel (150 g) eluting with 9:1 DCM/(chloroform:methanol:concentrated NH4OH 80:18:2) to obtain the desired intermediate (2.86 g, 91%). MS (APCI+) m/z: 225 (M+H)+.

Provenance & Evidence