Triacetoxyperiodinane → 1-Cycloheptyl-4,4-dimethyl-5-oxo-pyrrolidine-3-carbaldehyde

HRID 16208Notes

Reaction equation

HRID 16208 reaction equation
C([SiH2][O:6][C:7](C)(C)[CH:8]1[CH2:12][N:11]([CH:13]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[C:10](=[O:20])[C:9]1([CH3:22])[CH3:21])(C)(C)C.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>CO.Cl>[CH:13]1([N:11]2[C:10](=[O:20])[C:9]([CH3:21])([CH3:22])[CH:8]([CH:7]=[O:6])[CH2:12]2)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 1317270964-(Tert-butyl-dimethyl-silanyloxymethyl)-1-cycloheptyl-3,3-dimethyl-pyrrolidin-2-one

Product 1

HCID 870923081-Cycloheptyl-4,4-dimethyl-5-oxo-pyrrolidine-3-carbaldehyde

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

To a solution of Example 1D (0.168 mg, 0.475 mmoles) in methanol (1.5 mL), two drops of 12M HCl was added and stirred for one hour. The solvent was evaporated in vacuo. The residue was taken in dichloromethane (2.5 mL) and Dess-Martin periodinane (0.25 gm, 0.593 mmoles) was added and stirred at room temperature for two hours. The reaction was quenched with 10% sodium bisulfite and extracted with dichloromethane. The organic phase was washed with water, dried with MgSO4, filtered, and evaporated in vacuo to provide the title compound.

Workup

  1. customThe solvent was evaporated in vacuo
  2. stirringstirred at room temperature for two hours
  3. customThe reaction was quenched with 10% sodium bisulfite
  4. extractionextracted with dichloromethane
  5. washThe organic phase was washed with water
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-e58910d5be334e0b8fdc14a5c87f8aa6
Source dataset
uspto-grants-2010_06
Patent number
US07737137B2

Reaction notes

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