Triacetoxyperiodinane → 1-tert-Butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate

HRID 453228Notes

Reaction equation

HRID 453228 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([OH:10])[CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][C:8](=[O:10])[CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 51482991-Tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

Product 1

HCID 42518531-tert-Butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (5 g, 20.4 mmol) in DCM (100 mL), Dess-Martin periodinane (12.97 g, 30.6 mmol) is added. After completion of the reaction as judged by TLC the reaction is quenched with sat NaHCO3, washed with sat sodium thiosulfate and extracted with DCM. The organics are dried and evaporated and used crude in the next step.

Workup

  1. customAfter completion of the reaction
  2. customis quenched with sat NaHCO3
  3. washwashed
  4. extractionextracted with DCM
  5. customThe organics are dried
  6. customevaporated

Sources & evidence

ORD record
ord-e13b1c3956c44af9a862f6d94736961e
Source dataset
uspto-grants-2013_07
Patent number
US08492393B2

Reaction notes

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