Benzene → HCID 59541018, compound

HRID 1677549Notes

Reaction equation

HRID 1677549 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12](=[O:13])[C@H:11]3[C@@H:14]([Si](C)(C)C)[S:15][CH2:16][C@H:10]3[C:9]2=[O:21])[CH:5]=[CH:6][CH:7]=1.[F-].[Cs+].O.C1C=CC=CC=1>CN(P(N(C)C)(N(C)C)=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[C:9](=[O:21])[C@@H:10]3[CH2:16][S:15][CH2:14][C@@H:11]3[C:12]2=[O:13])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 241BenzeneHCID 962WaterHCID 25953Cesium fluorideHCID 59540573HCID 59540573, compound

Product 1

HCID 59541018HCID 59541018, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (3S,3aS,6aR)-5-(3-bromo-phenyl)-3-trimethylsilanyl-tetrahydro-thieno[3,4-c]pyrrole-4,6-dione (637 mg, 1.66 mmol) in HMPA (5 ml) and water (2 drops) was added powdered cesium fluoride (254 mg, 1.66 mmol). The mixture was heated (80° C., oil bath) for 8 hours and then stirred over night at ambient. Water (50 ml) and benzene (60 ml) were added and the material was shaken. The organic phase was collected and washed with brine (50 ml). The benzene phase was collected and the aqueous phase was back-extracted (2×40 ml) with benzene. The organics were combined, dried (MgSO4), filtered and stripped. The remainder was purified by silica gel chromatography eluting with 4% to 45% ethyl acetate in hexanes to afford 290 mg of (3aR,6aS)-5-(3-bromo-phenyl)-tetrahydro-thieno[3,4-c]pyrrole-4,6-dione, as a brown-yellow solid.

Workup

  1. stirringthe material was shaken
  2. customThe organic phase was collected
  3. washwashed with brine (50 ml)
  4. customThe benzene phase was collected
  5. extractionthe aqueous phase was back-extracted (2×40 ml) with benzene
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customThe remainder was purified by silica gel chromatography
  9. washeluting with 4% to 45% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-2af3019cb34d48598bcc8948b94a9b0c
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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