Methanol → HCID 53783690, compound

Participants

Reaction Steps

A 401 mg (2 mmol) sample of 3-(1-methyl4-hydroxymethyl-5-oxo-2(S)-pyrrolidinylmethoxy)pyridine, from step 48a above, was dissolved in 6 mL of THF and 6 mL of 1M B2H6 was added. The reaction mixture was heated at reflux for 2 hours, then stirred at room temperature for 15 minutes after methanol was added. The solvent was removed under pressure, and the residue was dissolved in 4 mL of ethanol. The this solution was added 251 mg of CsF, and the reaction mixture was heated at reflux for 16 hours. The solvent was removed, and the residue was purified on a column of silica gel, eluting with 100:5 to 10:1 chloroform:methanol 78 mg of a mixture of cis and trans product. cis compound: MS (DCI/NH3) m/e: 223 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ: 8.32 (m, 1H), 8.23 (t, 1H, J=3 Hz), 7.21 (m, 1H), 4.16-3.94 (m, 2H), 3.77-3.54 (m, 2H), 3.09-3.01 (m, 1H), 2.88-2.64 (m, 1H), 2.58-2.47 (m, 1H), 2.46 (m, 1H), 2.46 (s, 1H), 2.38-2.29 (m, 1H), 1.98-1.81 (m, 1H). trans compound: MS (DCI/NH3) m/e: 223 (M+H)+. 1H NMR (CDCl3, 300 MHz) d: 8.33 (m, 1H), 8.23 (m, 1H), 7.23 (m, 1H), 4.20-3.96 (m, 2H), 3.74-3.59 (m, 2H), 3.42-3.26 (m, 1H), 2.97-2.83 (m, 1H), 2.54 (s, 1H), 2.48-2.23 (m, 1H), 2.04-1.80 (m, 1H).

Provenance & Evidence