Tetrabutylammonium Fluoride → 114676-93-6

HRID 1029648Notes

Reaction equation

HRID 1029648 reaction equation
[Si]([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:11]([CH3:21])[CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:17]([O:16][C:14]([N:12]1[CH2:13][C@H:9]([OH:8])[CH2:10][C@H:11]1[CH3:21])=[O:15])([CH3:20])([CH3:18])[CH3:19]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 10979991HCID 10979991, compound

Product 1

HCID 14117010114676-93-6Yield 78.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (2R,4R)-4-(tert-butyldimethylsilyloxy)-1-(tert-butoxycarbonyl)-2-methylpyrrolidine (3.9 g) and tetrabutylammonium fluoride (1 Mol-tetrahydrofuran solution, 12.4 ml) in tetrahydrofuran (40 ml) was stirred at 0° C. for one hour. The reaction mixture was extracted with ethyl acetate, the organic layer was separated, washed with brine, and dried over magnesium sulfate. Evaporation of the solvent gave an oil, which was chromatographed on silica gel (200 ml) eluting with a mixture of hexane and ethyl acetate (1:1, V/V) to give (2R,4R)-1-(tert-butoxycarbonyl)-4-hydroxy-2-methylpyrrolidine (1.96 g).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. customthe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent
  6. customgave an oil, which
  7. customwas chromatographed on silica gel (200 ml)
  8. washeluting with a mixture of hexane and ethyl acetate (1:1, V/V)

Sources & evidence

ORD record
ord-015612b83f04488cb9bc254184cfd2bc
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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