Allyl bromide → HCID 54270696, compound

HRID 2396800Notes

Reaction equation

HRID 2396800 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([CH2:13][O:14][CH2:15][C@H:16]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[H-].[Na+].[CH2:35](Br)[CH:36]=[CH2:37]>CN(C=O)C>[F:1][C:2]([F:31])([F:32])[C:3]1[CH:4]=[C:5]([CH2:13][O:14][CH2:15][C@H:16]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:17]([C:18]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19])[CH2:37][CH:36]=[CH2:35])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 22859116HCID 22859116, compound

Product 1

HCID 54270696HCID 54270696, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-2-((3,5-Bis(trifluoromethyl)phenyl)methyloxy)-1-phenyl-1-(N-t-butoxycarbonylamino)ethane (1.1g, Example 2b) was dissolved in 20ml anhydrous DMF and sodium hydride (0.085g) was added. The reaction mixture was stirred for 20 min and allyl bromide (0.300g) added and stirred for a further 16h. The reaction was quenched by the addition of water (30ml) and poured into 100ml ethyl acetate. The organic layer was washed with water (3×20ml), brine and dried (MgSO4). The solvent was removed in vacuo and the residue chromatographed on silica eluting with 10% Ethyl acetate/hexane to give (S)-2-((3,5-bis(trifluoromethyl)phenyl)methyloxy)-1-phenyl-1-(N-t-butoxycarbonyl-N-allylamino)ethane as a colourless oil 0.980g. m/z=504 (M+H).

Workup

  1. stirringstirred for a further 16h
  2. customThe reaction was quenched by the addition of water (30ml)
  3. additionpoured into 100ml ethyl acetate
  4. washThe organic layer was washed with water (3×20ml), brine
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo
  7. customthe residue chromatographed on silica eluting with 10% Ethyl acetate/hexane

Sources & evidence

ORD record
ord-01fb96a3fe534a619814924e5a18b9ef
Source dataset
uspto-grants-1996_02
Patent number
US05494926

Reaction notes

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