Tetrahydrofuran → HCID 70980723, compound

HRID 1475384Notes

Reaction equation

HRID 1475384 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[C:14]([C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=C)[N:13]=[CH:12][C:11]=2[C:10]([CH3:26])([CH3:25])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C[O:30]CC1>CC(C)=O.O.O=[Os](=O)(=O)=O>[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[C:14]([C:17](=[O:30])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:13]=[CH:12][C:11]=2[C:10]([CH3:26])([CH3:25])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 8028TetrahydrofuranHCID 86723999HCID 86723999, compound

Product 1

HCID 70980723HCID 70980723, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of 3,3-dimethyl-6-(1-phenyl-vinyl)-2,3-dihydro-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (914 mg, 2.6 mmol) in THF (10 mL), acetone (5 mL) and water (5 mL) was added NaIO4 (2.8 g, 13.05 mmol), then OsO4 (2 mL of 4% solution in water, 0.3 mmol) and the reaction mixture was stirred at room temperature for 24 h. The reaction mixture was concentrated in vacuo, water (20 mL) was added and the product was extracted with EtOAc (2×20 mL). The organic phase was washed with brine, dried (MgSO4), filtered and the solvent evaporated. The crude product was purified by column chromatography on silica, eluted with petrol-EtOAc 0-40% to afford the title compound (654 mg, 65%). MS: [M+H]+=353.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo, water (20 mL)
  2. additionwas added
  3. extractionthe product was extracted with EtOAc (2×20 mL)
  4. washThe organic phase was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. customThe crude product was purified by column chromatography on silica
  9. washeluted with petrol-EtOAc 0-40%

Sources & evidence

ORD record
ord-1c1220a7e4c64febb58a2ea60833e238
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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