Trifluoroacetic acid → HCID 68157794, compound

Participants

Reaction Steps

To a solution of {(S)-1-[1-(tetrahydropyran-4-yl)-1H-benzoimidazol-2-yl]ethyl}carbamic acid tertbutyl ester (1.80 g, 5.22 mmol) in DCM (25 mL) was added TFA (10 mL) and the mixture was stirred at RT for 1 h. Volatiles were removed under reduced pressure and the resulting residue was partitioned between DCM and a saturated solution of NaHCO3. The aqueous phase was further extracted with DCM (×2) and the combined organic layers were dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM). The product containing fractions were concentrated in vacuo affording (S)-1-[1-(Tetrahydropyran-4-yl)-1H-benzoimidazol-2-yl]ethylamine as a light yellow solid (415 mg, 32%). LCMS: RT 0.27 min [M+Na]+ 268.1.

Provenance & Evidence