2-Bromo-5-(4-methoxy-benzyl)-3a,5,6,6a-tetrahydro-furo[2,3-c]pyrrol-4-one → 2-Bromo-3a,5,6,6a-tetrahydro-furo[2,3-c]pyrrol-4-one

HRID 1921845Notes

Reaction equation

HRID 1921845 reaction equation
[Br:1][C:2]1[O:19][CH:5]2[CH2:6][N:7](CC3C=CC(OC)=CC=3)[C:8](=[O:9])[CH:4]2[CH:3]=1>C(O)(C(F)(F)F)=O.C1(OC)C=CC=CC=1.C(OCC)(=O)C.C([O-])(O)=O.[Na+]>[Br:1][C:2]1[O:19][CH:5]2[CH2:6][NH:7][C:8](=[O:9])[CH:4]2[CH:3]=1

Participants

6

Reactant 1

HCID 590230372-Bromo-5-(4-methoxy-benzyl)-3a,5,6,6a-tetrahydro-furo[2,3-c]pyrrol-4-one

Product 1

HCID 590230212-Bromo-3a,5,6,6a-tetrahydro-furo[2,3-c]pyrrol-4-oneYield 78%

Reagents, catalysts & solvents 4

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 2-bromo-5-(4-methoxy-benzyl)-3a,5,6,6a-tetrahydro-furo[2,3-c]pyrrol-4-one (0.16 g, 0.498 mmol) in TFA (1.8 mL) and anisole (0.2 mL) is stirred at 80° C. for 2.5 hours. The reaction mixture is then diluted with ethyl acetate and neutralised with sat. NaHCO3. The aqueous layer is extracted with ethyl acetate (3×) and the combined organic layers are dried over MgSO4, filtered and concentrated in vacuo. The crude compound is purified by silica gel column chromatography eluting with 1:1 petroleum ether:ethyl acetate followed by 1:4 petroleum ether:ethyl acetate, to afford the title compound (79 mg, 78%).

Workup

  1. extractionThe aqueous layer is extracted with ethyl acetate (3×)
  2. dry with materialthe combined organic layers are dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude compound is purified by silica gel column chromatography
  6. washeluting with 1:1 petroleum ether

Sources & evidence

ORD record
ord-f8e00492374f4c9189c506cfd0ae4fbb
Source dataset
uspto-grants-2012_05
Patent number
US08173656B2

Reaction notes

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