Sodium periodate → tert-Butyl 5-formyl-1,3-dihydro-2H-isoindole-2-carboxylate

HRID 225613Notes

Reaction equation

HRID 225613 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH:17]=C)[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].I([O-])(=O)(=O)=[O:20].[Na+]>C1COCC1.O.C(OCC)(=O)C.[Os](=O)(=O)(=O)=O>[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH:17]=[O:20])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 2

HCID 23667635Sodium periodateHCID 57753717HCID 57753717, compound

Product 1

HCID 21250554tert-Butyl 5-formyl-1,3-dihydro-2H-isoindole-2-carboxylateYield 62%

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 3.79 mmol 5-vinyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester in 25 ml THF and 5 ml water were added 11.4 mmol sodium metaperiodate and 0.08 mmol osmium tetroxide solution (2.5% in tBuOH) and the mixture was stirred at RT for 2 h before being taken up in ethyl acetate and washed sequentially with water and brine. The organic phase was then dried over sodium sulfate and concentrated in vacuo. The residue was purified by chromatography (SiO2, heptane/ethyl acetate) to yield the title compound as a white solid (62% yield). MS (m/e): 192.1 ([M+H−Me2C═CH2]+, 100%).

Workup

  1. washwashed sequentially with water and brine
  2. dry with materialThe organic phase was then dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography (SiO2, heptane/ethyl acetate)

Sources & evidence

ORD record
ord-7f910dca5c394d2fb9282be6f244bea1
Source dataset
uspto-grants-2009_07
Patent number
US07557114B2

Reaction notes

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