Allyl bromide → HCID 66975335, compound

HRID 1022775Notes

Reaction equation

HRID 1022775 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@:9]2([CH2:23][OH:24])[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[H-].[Na+].[CH2:27](Br)[CH:28]=[CH2:29]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C@@:9]2([CH2:23][O:24][CH2:29][CH:28]=[CH2:27])[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 66974988HCID 66974988, compound

Product 1

HCID 66975335HCID 66975335, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl (7S)-7-(3,4-dichlorophenyl)-7-(hydroxymethyl)-1,4-oxazepane-4-carboxylate (1.01 g) in DMF (7 mL) was added sodium hydride (129 mg) at 0° C. After stirring for 10 min, allyl bromide (0.272 mL) was added, and the mixture was stirred at room temperature for 10 min. Under ice-cooling, the reaction was quenched with water, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate (0%-50%)) to give the title compound (917 mg) as a colorless oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 10 min
  2. temperatureUnder ice-cooling
  3. customthe reaction was quenched with water
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated
  8. customThe residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate (0%-50%))

Sources & evidence

ORD record
ord-412ebca6a22b4cb5972429a6d2d5c663
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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