Trifluoroacetic acid → HCID 68882130, compound

Participants

Reaction Steps

To an ice-cooled, rapidly stirred slurry of 4-hydroxy-4-(5-bromo-2-fluoro-4-methylthiophenyl)-N-Cbz-piperidine (7.82 g) in triethylsilane (19.7 g) was slowly added tri-fluoroacetic acid (18.6 g). When addition was complete the mixture was warmed to room temperature and stirred overnight (18 h). At the end of this period the mixture was poured into 100 mL saturated NaHCO3 and extracted with DCM. Extracts were combined, dried over Na2SO4, filtered, and concentrated under reduced pressure to give an oil. The product was purified by chromatography on silica (7:3, hexane:EtOAc) to give 5.18 g of an oil; MS m/z 438 (M+); 1H NMR (CDCl3) δ 7.45-7.30 (m), 7.25 (d), 6.80 (d), 5.15 (s), 4.50-4.20 (m), 3.11-2.80 (m), 1.90-1.48 (m).

Provenance & Evidence