Tert-butyl 3,4-dihydroxypyrrolidine-1-carboxylate → 1,1-Dimethylethyl N,N-bis(2-oxoethyl)carbamate

HRID 2354884Notes

Reaction equation

HRID 2354884 reaction equation
I([O-])(=O)(=O)=O.[Na+].[C:7]([O:11][C:12]([N:14]1[CH2:18][CH:17]([OH:19])[CH:16]([OH:20])[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>O.C1COCC1>[C:7]([O:11][C:12](=[O:13])[N:14]([CH2:18][CH:17]=[O:19])[CH2:15][CH:16]=[O:20])([CH3:10])([CH3:8])[CH3:9]

Participants

5

Reactant 2

HCID 13329884Tert-butyl 3,4-dihydroxypyrrolidine-1-carboxylateHCID 23667635Sodium periodate

Product 1

HCID 135745471,1-Dimethylethyl N,N-bis(2-oxoethyl)carbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium periodate (20.31 g, 94.96 mmol) in H2O (118 mL) was added to a cooled solution of 3,4-dihydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (19.3 g, 94.6 mmol) in THF (158 mL) over a 30 minute period. The resulting white suspension was allowed to stir at room temperature for 3 h. The suspension was filtered and the filtrate concentrated under vacuum to remove the THF. The resulting aqueous solution was used directly in the next reaction.

Workup

  1. filtrationThe suspension was filtered
  2. concentrationthe filtrate concentrated under vacuum
  3. customto remove the THF
  4. customThe resulting aqueous solution was used directly in the next reaction

Sources & evidence

ORD record
ord-d5257c58c1784844bea6b37a89cafe0f
Source dataset
uspto-grants-2010_07
Patent number
US07754712B2

Reaction notes

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