Dichloromethane → Ammonium Hydroxide

Participants

Reaction Steps

A 160 mg (0.5 mmol) sample of 3-(cis-1-BOC-3-propyl-2-pyrrolidinylmethoxy)pyridine, from step 60b above, was dissolved in 2 mL of methylene chloride and stirred with 1 mL of TFA for 16 hours at room temperature. The solvent was removed under vacuum, and the residue was adjusted to pH 8 with NaHCO3. The mixture was extracted with methylene chloride, and the extract was dried over MgSO4The residue was purified by chromatography on silica gel, eluting with 10:2:0.2 CHCl3 :methanol:ammonium hydroxide, to give 60 mg of the title product MS (DCI/NH3) m/e: 221 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ: 8.33 (m, 1H), 8.24 (m, 1H), 7.22 (m, 2H), 4.10 (m, 1H), 4.00 (m, 1H), 3.69 (m, 1H), 3.24 (m, 1H), 3.07 (m, 1H), 2.33 (m, 1H), 2.07 (m, 1H), 1.65 (m, 1H), 1.39 (m, 4H), 0.92 (m, 3H).

Provenance & Evidence