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

HRID 1666004Notes

Reaction equation

HRID 1666004 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-4520229419b54e41833a2846f9d9958c
Source dataset
uspto-grants-2011_10
Patent number
US08039622B2

Reaction notes

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