Benzyl Bromide → HCID 19705562, compound

HRID 727545Notes

Reaction equation

HRID 727545 reaction equation
[CH3:1][CH:2]([CH3:21])[CH2:3][C:4]1([CH:10]([C:18]([CH3:20])=[CH2:19])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8][CH2:7][NH:6][C:5]1=[O:9].[H-].[Na+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1COCC1>[CH3:1][CH:2]([CH3:21])[CH2:3][C:4]1([CH:10]([C:18]([CH3:20])=[CH2:19])[C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])[CH2:8][CH2:7][N:6]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:5]1=[O:9]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 19705548HCID 19705548, compound

Product 1

HCID 19705562HCID 19705562, compoundYield 117.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A cold (0° C.) solution of tert-butyl 3-(2-methylpropyl)-2-oxo-α-(propen-2-yl)-3-pyrrolidineacetate (1.11 g, 3.76 mmol) in dry THF (25 mL) is treated with NaH (60% dispersion in mineral oil, 226 mg, 5.64 mmol) in one portion. After 30 minutes, benzyl bromide (537 μL, 4.51 mmol) is added. The solution is allowed to slowly warm to room temperature, stirring under N2 overnight. The mixture is quenched with H2O (25 mL) and extracted with EtOAc (3×25 mL). The organic extracts are combined, washed with brine (25 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to yield 1.70 g of yellow oil. The oil is purified by silica gel chromatography (30 g SG, 10% EtOAc/hexane) to give 1.37 g (94%) of the title compound as a clear, colorless oil.

Workup

  1. customThe mixture is quenched with H2O (25 mL)
  2. extractionextracted with EtOAc (3×25 mL)
  3. washwashed with brine (25 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fb08a005b27b4eefa167f0a4e2443dc9
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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