Tetrabutylammonium Fluoride → (4R)-1-[(6-bromopyridin-2-yl)methyl]-4-hydroxypyrrolidin-2-one

HRID 385840Notes

Reaction equation

HRID 385840 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]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59525625(4R)-1-[(6-Bromopyridin-2-yl)methyl]-4-{[tert-butyl(dimethyl)silyl]oxy}pyrrolidin-2-one

Product 1

HCID 59526275(4R)-1-[(6-bromopyridin-2-yl)methyl]-4-hydroxypyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-54d2202d4cfe4e1686764915b555f412
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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