Formaldehyde → Trifluoroacetic acid

Participants

Reaction Steps

To a solution of N-(2-{(3S)-3-[(4-hydroxy-4-pyridin-2-ylcyclohexyl)amino]pyrrolidin-1-yl}-2-oxoethyl)-3-(trifluoromethyl)benzamide (49 mg, 0.1 mmol) and formaldehyde (0.3 mL, 37% water solution) in THF (2 mL) was added Na(OAc)3BH (64 mg, 0.3 mmol). After being stirred at room temperature overnight, the reaction was quenched by addition of a saturated NaHCO3 solution. The resulting solution was extracted with EtOAc and the EtOAc layer was dried (MgSO4) and concentrated. Purification by prep HPLC provided the title compound as a TFA salt. MS (M+H)+ 505.

Provenance & Evidence