Acetic Acid → HCID 89726588, compound

Participants

Reaction Steps

To a solution of (4,5,6,7-tetrahydro-imidazo[4,5-c]pyridin-1-yl)-acetic acid benzyl ester (176 mg) in MeOH was added formaldehyde (36.5% in water, 0.052 mL) followed by NaBH3CN (29 mg) and AcOH (0.5 mL). The reaction mixture was stirred at RT overnight. DCM was added and the mixture was washed with sat. NaHCO3. The aq. layer was extracted with DCM, the combined org. layers were dried (MgSO4), filtered off and evaporated to dryness. The residue was purified by CC (Biotage, SNAP 10 g cartridge, solvent A: DCM; solvent B: DCM/MeOH 8/2; gradient in % B: 25 for 3CV, 25 to 50 over 2CV, 50 for 5CV, 50 to 100 over 3CV, 100 for 2CV) to afford (5-methyl-4,5,6,7-tetrahydro-imidazo[4,5-c]pyridin-1-yl)-acetic acid benzyl ester (39 mg, yellow oil). LC-MS (B): tR=0.46 min; [M+H]+: 286.16.

Provenance & Evidence