Tetrabutylammonium Fluoride → HCID 86618698, compound

HRID 2239377Notes

Reaction equation

HRID 2239377 reaction equation
[Si]([O:8][CH2:9][C:10]1[N:15]=[C:14]([O:16][CH2:17][C@H:18]2[CH2:22][CH2:21][CH2:20][N:19]2[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:13]=[CH:12][CH:11]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:8][CH2:9][C:10]1[N:15]=[C:14]([O:16][CH2:17][C@H:18]2[CH2:22][CH2:21][CH2:20][N:19]2[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86618697HCID 86618697, compound

Product 1

HCID 86618698HCID 86618698, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl (2R)-2-({[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-yl]oxy}methyl)pyrrolidine-1-carboxylate (604 mg, 1.4 mmol) was dissolved in THF (5 mL) and tetrabutylammonium fluoride (2.1 mL, 1.0M in THF, 2.1 mmol) was added. The reaction mixture was stirred 1 h. The organic solvent was evaporated and the residue purified by flash chromatography using a gradient of EtOAc/heptane to give the title compound as a clear oil. Yield: 430 mg (97%). MS (ESI+) 309.3 (M+1H+).

Workup

  1. customThe organic solvent was evaporated
  2. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-bf2066e7a69041d2a3bdbaf779404ee5
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

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