Benzyl Bromide → HCID 69797921, compound

HRID 1063420Notes

Reaction equation

HRID 1063420 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:7][O:6][C:5](=[O:8])[CH:4]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C)C=O>[CH2:21]([N:1]([CH2:2][CH:3]1[CH2:7][O:6][C:5](=[O:8])[CH:4]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:4][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 69797124HCID 69797124, compound

Product 1

HCID 69797921HCID 69797921, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

(3RS, 4RS) 4-Aminomethyl-3-phenyl-dihydrofuran-2-one (2.15 g, 0.011 mol) was added to potassium carbonate (15.5 g), benzyl bromide (6.69 ml) and dimethylformamide (10 ml) and stirred for 3 hours at 50° C. dimethylformamide was removed in vacuo and the reaction was dispersed between ethyl acetate (40 ml) and water (60 ml), the aqueous phase was washed with ethyl acetate (2×30 ml) and the organic layers were combined and washed with brine solution (100 ml) and dried over MgSO4. The solvent was removed in vacuo and purified by flash column chromatography on silica gel and eluting in increasing concentrations of ethyl aceate in hexane (5-50%) to give the title compound (1.15 g, 46%).

Workup

  1. customwas removed in vacuo
  2. additionthe reaction was dispersed between ethyl acetate (40 ml) and water (60 ml)
  3. washthe aqueous phase was washed with ethyl acetate (2×30 ml)
  4. washwashed with brine solution (100 ml)
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed in vacuo
  7. custompurified by flash column chromatography on silica gel
  8. washeluting
  9. temperaturein increasing concentrations of ethyl aceate in hexane (5-50%)

Sources & evidence

ORD record
ord-3795fd2b044f444c81baa08832c1cb6a
Source dataset
uspto-grants-2005_11
Patent number
US06964981B2

Reaction notes

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