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

HRID 1971430Notes

Reaction equation

HRID 1971430 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-9d441012b33942a9a2266f1730f24f2d
Source dataset
uspto-grants-2013_04
Patent number
US08431584B2

Reaction notes

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