Sodium Azide → (2S,4S)-1-tert-butyl 2-methyl 4-azidopyrrolidine-1,2-dicarboxylate

HRID 2063940Notes

Reaction equation

HRID 2063940 reaction equation
[C:1]([N:8]1[CH2:12][C@H:11](OS(C)(=O)=O)[CH2:10][C@H:9]1[C:18]([O:20][CH3:21])=[O:19])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[N-:22]=[N+:23]=[N-:24].[Na+]>CN(C=O)C>[C:1]([N:8]1[CH2:12][C@@H:11]([N:22]=[N+:23]=[N-:24])[CH2:10][C@H:9]1[C:18]([O:20][CH3:21])=[O:19])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 147726821-tert-Butyl 2-methyl (2S,4R)-4-((methanesulfonyl)oxy)pyrrolidine-1,2-dicarboxylate

Product 1

HCID 11219435(2S,4S)-1-tert-butyl 2-methyl 4-azidopyrrolidine-1,2-dicarboxylateYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Methyl (2S,4R)-1-Boc-4-[(methylsulfonyl)oxy]pyrrolidine-2-carboxylate (9 g, 27.86 mmol) obtained in Step C was dissolved in DMF (80 ml) and NaN3 (2.7 g, 41.79 mmol) was added thereto and stirred at 90° C. for 10 hours. The reaction mixture was concentrated in vacuo, extracted with EtOAc. The organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography (eluent, EtOAc/Hex=1/4) to give the title compound (6 g, 80%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. extractionextracted with EtOAc
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (eluent, EtOAc/Hex=1/4)

Sources & evidence

ORD record
ord-f1fedf14efcf4eebbded4e0108ec4dcd
Source dataset
uspto-grants-2012_10
Patent number
US08288386B2

Reaction notes

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