Tetrabutylammonium Fluoride → HCID 57297236, compound

HRID 1078724Notes

Reaction equation

HRID 1078724 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][Si](C(C)(C)C)(C)C)[CH2:10][C@H:9]1[C@H:21]([OH:27])[CH2:22][C:23]([O:25][CH3:26])=[O:24])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[C@H:21]([OH:27])[CH2:22][C:23]([O:25][CH3:26])=[O:24])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 10862338HCID 10862338, compound

Product 1

HCID 57297236HCID 57297236, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (2S,4R)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-[(R)-1-hydroxy-2-(methoxycarbonyl)ethyl]pyrrolidine (2.40 g, 5.95 mmol) in tetrahydrofuran (24 ml) was dropwise added a 1M tetrabutylammonium fluoride--tetrahydrofuran solution (7.14 ml) at room temperature. The mixture was stirred at the same temperature for 4 h. The reaction solution was washed with saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography (heptane-ethyl acetate=3:7) to obtain (2S,4R)-N-tert-butoxycarbonyl-4-hydroxy-2-[(R)-1-hydroxy-2-(methoxycarbonyl)ethyl]pyrrolidine diastereomer B (1.22 g, yield: 70.9%). ##STR399##

Workup

  1. customat room temperature
  2. washThe reaction solution was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed in vacuo
  5. customThe residue was purified by silica gel column chromatography (heptane-ethyl acetate=3:7)

Sources & evidence

ORD record
ord-fa6c63fe14bc471d961b793f1a4fa141
Source dataset
uspto-grants-1996_08
Patent number
US05550121

Reaction notes

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