Sodium hydride → HCID 19988987, compound

HRID 973700Notes

Reaction equation

HRID 973700 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]2[CH2:14][NH:13][C:12](=[O:15])[CH2:11]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[H-].[Na+].[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:10]2[CH2:14][N:13]([Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[C:12](=[O:15])[CH2:11]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 19988976HCID 19988976, compound

Product 1

HCID 19988987HCID 19988987, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

Under nitrogen, 540 mg (2 mmol) of 4-(3-bromo-4-methoxyphenyl)pyrrolidin-2-one in 10 ml of dimethylformamide is combined with 60 mg (2 mmol) of sodium hydride. After 20 minutes of stirring, after cooling to 0° C., 300 mg (2 mmol) of tert-butyldimethylsilyl chloride in 5 ml of dimethylformamide is added dropwise and the mixture stirred at 0° C. for 30 minutes as well as at room temperature for 30 minutes. After concentration, the mixture is distributed in ethyl acetate/water. The ethyl acetate phase is dried, filtered and concentrated and the residue is chromatographed over silica gel with methylene chloride:ethanol=10:1 as the eluent, thus obtaining 420 mg of 4-(3-bromo-4-methoxyphenyl)-1-tert-butyldimethylsilylpyrrolidin-2-one, mp 150°-152° C.

Workup

  1. stirringthe mixture stirred at 0° C. for 30 minutes as well as at room temperature for 30 minutes
  2. concentrationAfter concentration
  3. dry with materialThe ethyl acetate phase is dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue is chromatographed over silica gel with methylene chloride

Sources & evidence

ORD record
ord-a42a0ef168e94db8b958f6c1a39a285c
Source dataset
uspto-grants-1991_11
Patent number
US05064854

Reaction notes

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