Methyl iodide → 4-Benzyl-5-bromo-2-[(3r,4r)-3-hydroxy-4-methoxypyrrolidine-1-yl]pyridine

반응식

[H-].[Na+].[CH3:3]I.[CH2:5]([C:12]1[C:17]([Br:18])=[CH:16][N:15]=[C:14]([N:19]2[CH2:23][C@@H:22]([OH:24])[C@H:21]([OH:25])[CH2:20]2)[CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>O1CCCC1>[CH2:5]([C:12]1[C:17]([Br:18])=[CH:16][N:15]=[C:14]([N:19]2[CH2:20][C@@H:21]([O:25][CH3:3])[C@H:22]([OH:24])[CH2:23]2)[CH:13]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

참가 물질

실험 절차

190 mg of 60% oily sodium hydride and 0.3 ml of methyl iodide were added to a solution of 1.67 g of 4-benzyl-5-bromo-2-[(3R,4R)-3,4-dihydroxypyrrolidine-1-yl]pyridine in tetrahydrofuran, followed by stirring for 6 hours. Then, the reaction solution was extracted with ethyl acetate-water, and the organic phase was washed with water and brine, dried over anhydrous magnesium sulfate and evaporated. The residue was subjected to silica gel column chromatography and eluted with 50% ethyl acetate, to give 560 mg of the target compound.