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

HRID 2115606Notes

Reaction equation

HRID 2115606 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-2a119d7d5c6e408480ce77fa6f411c06
Source dataset
uspto-grants-2008_10
Patent number
US07435833B2

Reaction notes

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