Pyridine → benzyl (2S)-2-formyl-2-methylpyrrolidine-1-carboxylate

HRID 1010913Notes

Reaction equation

HRID 1010913 reaction equation
[OH:1][CH2:2][C@:3]1([CH3:18])[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].N1C=CC=CC=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH:2]([C@:3]1([CH3:18])[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])=[O:1]

Participants

6

Reactant 4

HCID 1049PyridineHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 67312716HCID 67312716, compound

Product 1

HCID 86625219benzyl (2S)-2-formyl-2-methylpyrrolidine-1-carboxylateYield 92.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution obtained by dissolving 377 mg of the compound [63-2] and 147 mg of pyridine in 7.5 mL of chloroform, 673 mg of Dess-Martin periodinane was added at room temperature, and the mixture was heated under reflux for 1 hour. To the reaction solution, a saturated aqueous sodium thiosulfate solution was added, and the mixture was extracted with chloroform. The obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine, sequentially, and dried over anhydrous sodium sulfate. The insolubles were filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate 100/0 to 60/40) to obtain 346 mg of benzyl (2S)-2-formyl-2-methylpyrrolidine-1-carboxylate [63-3] (hereinafter, referred to as the compound [63-3].

Workup

  1. customTo a solution obtained
  2. additionwas added at room temperature
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 1 hour
  5. extractionthe mixture was extracted with chloroform
  6. washThe obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine
  7. dry with materialsequentially, and dried over anhydrous sodium sulfate
  8. filtrationThe insolubles were filtered
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate 100/0 to 60/40)

Sources & evidence

ORD record
ord-672c5b1961674a00b40fb6a2427e2a21
Source dataset
uspto-grants-2011_07
Patent number
US07977336B2

Reaction notes

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