Hydrochloric Acid → HCID 53855103, compound

Participants

Reaction Steps

(S)-1-t-Butoxycarbonyl-2-pyrrolidinemethanol (2.01 g, 10.0 mmol, prepared in Example 15a) and 5-chloro-3-pyridinol (1.454 g, 11.0 mmol, Aldrich Chemical Co.). were allowed to react in the presence of triphenylphosphine and DEAD as described in Example 2a. The crude product was hydrolyzed with 10% HCl at room temperature for 0.5 hours. The solution was made basic with NaHCO3, then extracted with ethyl acetate. After removal of the solvent, the residue was purified by chromatography over silica gel to give 166.5 mg of the title product. MS (DCI/NH3) m/e: 213 (M+H)+ and 215 (M+H)+. 1H NMR (CDCl3, 300MHz) δ: 7.99 (d, J=5.1 Hz, 1H), 7.25 (d, J=8.5 Hz, 1H), 7.20 (dd, J=5.1, 8.5 Hz), 1H), 4.08-4.01 (m, 1H), 4.40-3.94 (m, 1H), 3.69-3.58 (m, 1H), 3.15-2.98 (m, 2H), 2.07-1.61 (m, 4H).

Provenance & Evidence