Tetrabutylammonium Fluoride → (4R)-1-[(6-bromopyridin-2-yl)methyl]-4-hydroxypyrrolidin-2-one
Reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH2:8][N:9]2[CH2:13][C@H:12]([O:14][Si](C(C)(C)C)(C)C)[CH2:11][C:10]2=[O:22])[CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[Br:1][C:2]1[N:7]=[C:6]([CH2:8][N:9]2[CH2:13][C@H:12]([OH:14])[CH2:11][C:10]2=[O:22])[CH:5]=[CH:4][CH:3]=1Participants
4
Procedure
(4R)-1-[(6-Bromopyridin-2-yl)methyl]-4-{[tert-butyl(dimethyl)silyl]oxy}pyrrolidin-2-one was dissolved in tetrahydrofuran (33.4 mL), and tetrabutylammonium fluoride (5.84 mL, 5.84 mmol) was added dropwise and the solution stirred at ambient temperature for five minutes. The reaction mixture was concentrated and purified by silica gel chromatography to yield the title compound.