Tetrabutylammonium Fluoride → tert-Butyl(3S)-3-hydroxymethyl-4-methyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate

HRID 446117Notes

Reaction equation

HRID 446117 reaction equation
[Si]([O:8][CH2:9][C@:10]1([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:14]([CH3:15])[C:13](=[O:16])[N:12]([C@@H:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH3:18])[CH2:11]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:8][CH2:9][C@:10]1([C:25]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26])[CH:14]([CH3:15])[C:13](=[O:16])[N:12]([C@@H:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH3:18])[CH2:11]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57758739tert-Butyl(3S)-3-{[tert-butyl(dimethyl)silyloxy]methyl}-4-methyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate

Product 1

HCID 57758675tert-Butyl(3S)-3-hydroxymethyl-4-methyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylateYield 67.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tert-butyl (3S)-3-{[tert-butyl (dimethyl) silyloxy]methyl}-4-methyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate (3.72 g, 8.31 mmol) was dissolved in tetrahydrofuran (70 mL), and tetrabutylammonium fluoride (12.5 mL, 1.0 mol/l solution in tetrahydrofuran, 12.5 mmol) was added dropwise in an ice bath. The mixture was stirred at the same temperature for 1 hour. After concentrating the mixture, saturated aqueous solution of ammonium chloride (200 mL) was added, and the mixture was extracted with ethyl acetate (200 mL×2). The organic layer was washed with saturated aqueous solution of sodium chloride (100 mL), and dried with anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (elusion by hexane:ethyl acetate=3:1→1:2) to obtain 1.87 g (67%) of the title compound as a white solid.

Workup

  1. concentrationAfter concentrating the mixture, saturated aqueous solution of ammonium chloride (200 mL)
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate (200 mL×2)
  4. washThe organic layer was washed with saturated aqueous solution of sodium chloride (100 mL)
  5. dry with materialdried with anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe concentrate was purified by silica gel column chromatography (elusion by hexane:ethyl acetate=3:1→1:2)

Sources & evidence

ORD record
ord-2c27bb760fab42ffb3ea3d1889037a19
Source dataset
uspto-grants-2013_07
Patent number
US08476429B2

Reaction notes

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