Ethyl Acetate → 2-Benzyloxycarbonylamino-1-phenyl-3,4-epoxy-butane

HRID 896574Notes

Reaction equation

HRID 896574 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH:20]=[CH2:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:27].CCOC(C)=O>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH:20]1[O:27][CH2:21]1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 70297m-Chloroperbenzoic acidHCID 136065862-Benzyloxycarbonylamino-1-phenyl-3-butene

Product 1

HCID 148872432-Benzyloxycarbonylamino-1-phenyl-3,4-epoxy-butane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-benzyloxycarbonylamino-1-phenyl-3-butene (1.43 g, 5.08 mmoles) in 20 mL of CH2Cl2 was added 3-chloroperoxybenzoic acid (2.19 g, 60%, 7.62 mmoles) in several portions, and the mixture was stirred at room temperature for 30 hrs. After addition of EtOAc (60 mL), the mixture was washed with saturated NaHCO3 and brine, and the organic layer was dried over Na2SO4. Evaporation of the solvent afforded an oily residue. The crude product was purified by column chromatography on silica gel with elution by 2:8 EtOAc-hexane to give pure 2-benzyloxycarbonylamino-1-phenyl-3,4-epoxy-butane. Part C: Preparation of 2-benzyloxycarbonylamino-4-[4-(4-fluorophenyl)methyl-1-piperidinyl]-1-phenyl-butan-3-ol.

Workup

  1. washthe mixture was washed with saturated NaHCO3 and brine
  2. dry with materialthe organic layer was dried over Na2SO4
  3. customEvaporation of the solvent
  4. customafforded an oily residue
  5. customThe crude product was purified by column chromatography on silica gel with elution by 2:8 EtOAc-hexane

Sources & evidence

ORD record
ord-67363d634e404229983ff212c1018b4b
Source dataset
uspto-grants-2005_07
Patent number
US06919368B2

Reaction notes

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