Water → HCID 59371410, compound

Participants

Reaction Steps

Trifluoroacetic acid (1.6 mL) and water (0.16 mL) were added to 8 mL of CH2Cl2. This mixture was added to 3-[[1-(tert-butoxycarbonyl)-2(R)-azetidinyl]methoxy]-5-[3-(2(S)-methoxy-3-phenylpropyl)phenyl]pyridine (470 mg, 0.96 mmol) at 0° C. under N2. The solution was stirred overnight at room temperature. After concentration in vacuo, the crude product (300 mg) was purified by preparative HPLC (column: SunFire Prep C18, 150×19, 5 μm; UV detection, at 254 nm; mobile phase: A, water with 0.05% CF3COOH; B, CH3CN; 18-40% B in A in 6 min, 40-100% in 1 min). The product-containing eluate was partially evaporated under reduced pressure (bath 30° C.) to remove CH3CN. The pH of the residue was adjusted to 8.0 with saturated aqueous NaHCO3 solution, and the product was extracted into EtOAc (3×60 mL). The combined organic phases were washed with brine and dried over Na2SO4. After filtration and concentration, the free amine (175 mg, 47%) was obtained as a colorless oil. LC-MS (ESI) m/z 389 (M+H+).

Provenance & Evidence