Methanol → HCID 71226920, compound

Participants

Reaction Steps

To a solution of 4-((S)-3-((1R,2R)-2-aminocyclohexylamino)piperidin-1-yl)benzonitrile (70 mg, 0.235 mmol) in MeOH (1 mL) at was added BF3.OEt2 (0.2 mL, 1.578 mmol) at rt. The reaction was stirred at reflux for 16 h. LC/MS showed only ˜22% of the desired products formed. More BF3.OEt2 (100 μL, 0.789 mmol) was added. The reaction was stirred at reflux for another 6 days. The reaction mixture was concentrated. The residue was diluted with EtOAc, washed with saturated aq NaHCO3, saturated aq NaCl solution. The organic extracts were concentrated under vacuum to give the crude product methyl 4-((S)-3-((1R,2R)-2-aminocyclohexylamino)piperidin-1-yl)benzoate (78 mg, 0.235 mmol, 100% yield). The product was used without further purification.

Provenance & Evidence