1-Acetoxy-2-bromoethane → HCID 67490873, compound

HRID 1917393Notes

Reaction equation

HRID 1917393 reaction equation
[C:1]([O:5][C:6]([C@@:8]1([CH2:22][OH:23])[CH2:12][C:11](=[O:13])[N:10]([C@@H:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:24]([O:27][CH2:28][CH2:29]Br)(=[O:26])[CH3:25].[H-].[Na+].[Cl-].[NH4+]>O1CCCC1>[C:1]([O:5][C:6]([C@@:8]1([CH2:22][O:23][CH2:25][C:24]([O:27][CH2:28][CH3:29])=[O:26])[CH2:12][C:11](=[O:13])[N:10]([C@@H:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 135641-Acetoxy-2-bromoethaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 57758657HCID 57758657, compound

Product 1

HCID 67490873HCID 67490873, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(3S)-3-Hydroxymethyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester (2.0 g, 6.26 mmol) and bromoethyl acetate (2.09 g, 12.52 mmol) were dissolved in tetrahydrofuran (40 mL). Sodium hydride (0.33 g, 7.51 mmol) was added at 0° C., and the mixture was stirred at room temperature for 18 hours. A saturated ammonium chloride solution (100 mL) was added to the reaction solution at 0° C., followed by extraction with ethyl acetate (300 mL). The organic layer was washed with water (100 mL) and brine (100 mL) and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (40% ethyl acetate/hexane) to give 1.74 g of the title compound as a colorless oil.

Workup

  1. extractionfollowed by extraction with ethyl acetate (300 mL)
  2. washThe organic layer was washed with water (100 mL) and brine (100 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3f493d65301a40978e289db68f50472e
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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