Water → HCID 67406569, compound

HRID 1372624Notes

Reaction equation

HRID 1372624 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([F:13])[CH2:10][C@H:9]1[CH2:14][OH:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:18]([O:25][CH2:26]/[CH:27]=[CH:28]\[CH2:29]Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:18]([O:25][CH2:26]/[CH:27]=[CH:28]\[CH2:29][O:15][CH2:14][C@@H:9]1[CH2:10][C@H:11]([F:13])[CH2:12][N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 5314571HCID 5314571, compoundHCID 58980888HCID 58980888, compound

Product 1

HCID 67406569HCID 67406569, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of (2S,4S)-1-(tert-butoxycarbonyl)-4-fluoro-2-pyrrolidinylmethanol (2.46 g, 11.2 mmol) in THF (100 ml), sodium hydride (60% in oil; 896 mg, 22.4 mmol) was added in portions under stirring at 0° C. in a nitrogen gas stream. After stirring at the same temperature for 20 minutes, a solution of (Z)-4-benzyloxy-1-bromo-2-butene (2.76 g, 11.2 mmol) in THF (100 ml) was added. The reaction mixture was stirred for 5 minutes. To the reaction mixture was added tetra-n-butyl ammonium iodide (100 mg, 0.27 mmol) at 0° C. and the mixture was stirred for 15 minutes. The reaction mixture was stirred further at room temperature for 19 hours. Water (50 ml) was added while stirring the reaction mixture under ice cooling, followed by extraction with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (silica gel: 120 g), whereby from hexane/ethyl acetate (4/1) eluate fractions, the title compound (3.30 g, 78%) was obtained as a colorless oil.

Workup

  1. stirringAfter stirring at the same temperature for 20 minutes
  2. stirringThe reaction mixture was stirred for 5 minutes
  3. stirringthe mixture was stirred for 15 minutes
  4. stirringThe reaction mixture was stirred further at room temperature for 19 hours
  5. stirringwhile stirring the reaction mixture under ice cooling
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe extract was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationdistilled under reduced pressure
  10. customto remove the solvent
  11. customThe residue was purified by chromatography on a silica gel column (silica gel: 120 g), whereby from hexane/ethyl acetate (4/1) eluate fractions

Sources & evidence

ORD record
ord-7f7e01fdd503413cbb04defada4f380f
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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