Allyl bromide → (3S,4S)-4-Allyl-5-oxo-1-[(1R)-1-phenylethyl]-3-vinylpyrrolidine-3-carboxylic acid tert-butyl ester

HRID 1917360Notes

Reaction equation

HRID 1917360 reaction equation
[C:1]([O:5][C:6]([C@@:8]1([CH:22]=[CH2:23])[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].[CH2:24](Br)[CH:25]=[CH2:26].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[Cl-].[NH4+]>O1CCCC1>[C:1]([O:5][C:6]([C@@:8]1([CH:22]=[CH2:23])[C@H:12]([CH2:26][CH:25]=[CH2:24])[C:11](=[O:13])[N:10]([C@@H:14]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH3:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 67490859(3R)-5-Oxo-1-[(1R)-1-phenylethyl]-3-vinylpyrrolidine-3-carboxylic acid tert-butyl ester

Product 1

HCID 67490978(3S,4S)-4-Allyl-5-oxo-1-[(1R)-1-phenylethyl]-3-vinylpyrrolidine-3-carboxylic acid tert-butyl esterYield 50.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(3R)-5-oxo-1-[(1R)-1-phenylethyl]-3-vinylpyrrolidine-3-carboxylic acid tert-butyl ester (236.0 mg, 0.75 mmol) and allyl bromide (271.6 mg, 2.24 mmol) were dissolved in tetrahydrofuran. A 1 M solution of lithium hexamethyldisilazide in tetrahydrofuran (1.12 mL, 1.12 mmol) was added dropwise in a nitrogen atmosphere at 0° C. After stirring for 1.5 hours, a saturated ammonium chloride solution was added, followed by extraction with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and filtered. The solvent was evaporated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography (10% ethyl acetate/hexane) to give 135 mg of the title compound as a colorless oil.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-33243f2c2711457597a11d4f4ba6eb54
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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