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

HRID 1393220Notes

Reaction equation

HRID 1393220 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-fbd80dc37e274bbfb9e3917466f10d91
Source dataset
uspto-grants-2008_03
Patent number
US07345056B2

Reaction notes

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