Water → 3-[(2(S)-Azetidinyl)methoxy]-5-[4-[2-(benzyloxy)ethyl]phenyl]pyridine Trifluoroacetate

Participants

Reaction Conditions

Reaction Steps

Trifluoroacetic acid (1.0 mL) and water (0.11 mL) were added to CH2Cl2 (5.5 mL). This mixture was added to 3-[4-[2-(benzyloxy)ethyl]phenyl]-5-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]pyridine (220 mg, 0.46 mmol) in a 25 mL round-bottom flask with a magnetic stirrer under N2. After stirring at 30° C. for 24 h, TLC analysis indicated that the starting material had disappeared. The reaction mixture was concentrated, and the residue was purified by preparative HPLC (SunFire Prep C18 column, 19×150 mm, 5 μm particle size; UV detection at 254 nm; flow 15 mL/min; CH3CN/water gradient with addition of 0.05% CF3COOH, from 20-40% CH3CN in 6 min) to provide the title compound (140 mg, light-yellow solid) as a partial trifluoroacetate.

Provenance & Evidence