Acetic Acid → HCID 178445678, compound

Participants

Reaction Steps

To a suspension of 2′-fluoro-4′-formylbiphenyl-3-carboxylic acid amide (Preparation 9, 252 mg, 1.0 mmol) in DCM (100 mL) was added 4-tert-butylcyclohexylamine (500 μL, 3.2 mmol), acetic acid (200 μL, 3.5 mmol) and sodium triacetoxyborohydride (648 mg, 3.1 mmol). The mixture was stirred at rt for 16 h. EtOAc (100 mL) was added and the organics washed with aqueous NaHCO3 (30 mL), brine (30 mL) and dried (MgSO4). The solvent was removed in vacuo and the residue purified by column chromatography (17% EtOH: Toluene) to give cis-4′-[(4-tert-butylcyclohexylamino)methyl]-2′-fluorobiphenyl-3-carboxylic acid amide: RT=2.84 min; m/z (ES+)=383.0 [M+H]+, and trans-4′-[(4-tert-butylcyclohexylamino)methyl]-2′-fluorobiphenyl-3-carboxylic acid amide: RT=2.87 min; m/z (ES+)=383.0 [M+H]+.

Provenance & Evidence