Tetrahydrofuran → (1R,2S)-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-formyl-1-{2-[4-(trifluoromethyl)phenyl]ethyl}butyl formate

HRID 2410431Notes

Reaction equation

HRID 2410431 reaction equation
I([O-])(=O)(=O)=O.[Na+].[OH:7][C@@H:8]1[C@H:12]([OH:13])[O:11][C@H:10]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)[C@@H:9]1[CH2:26][CH2:27][N:28]1[C:36](=[O:37])[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]1=[O:38].O1CCCC1>CO>[CH:12]([O:11][C@H:10]([CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:23])([F:25])[F:24])=[CH:18][CH:17]=1)[C@@H:9]([CH:8]=[O:7])[CH2:26][CH2:27][N:28]1[C:36](=[O:37])[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]1=[O:38])=[O:13]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 23667635Sodium periodateHCID 67183312HCID 67183312, compound

Product 1

HCID 86700972(1R,2S)-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-formyl-1-{2-[4-(trifluoromethyl)phenyl]ethyl}butyl formate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of sodium metaperiodate (0.313 g in 1 mL of water) was added to a solution of the compound obtained from step f above (0.22 g) in methanol:tetrahydrofuran (3 mL:1 mL) at 0° C. The reaction mixture was stirred for 2 hours at same temperature. After stirring the reaction mixture for an additional 6 hours at room temperature, the reaction mixture was evaporated on a rotary evaporator, and the residue was taken into water and extracted with ethyl acetate. The organic layer was washed with water and brine solution, and dried over anhydrous sodium sulphate. The solvent was evaporated under reduced pressure to afford the title compound (0.22 g).

Workup

  1. customat 0° C
  2. stirringAfter stirring the reaction mixture for an additional 6 hours at room temperature
  3. customthe reaction mixture was evaporated on a rotary evaporator
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water and brine solution
  6. dry with materialdried over anhydrous sodium sulphate
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-637417b8635d411ab22079f41dae7c16
Source dataset
uspto-grants-2014_08
Patent number
US08816073B2

Reaction notes

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