Sodium Azide → 1-Tert-butyl 2-methyl 4-azidopyrrolidine-1,2-dicarboxylate

HRID 490584Notes

Reaction equation

HRID 490584 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8](I)[CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4].[N-:18]=[N+:19]=[N-:20].[Na+]>CN(C=O)C>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([N:18]=[N+:19]=[N-:20])[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 33557Sodium AzideHCID 675472144-Iodo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Product 1

HCID 147726831-Tert-butyl 2-methyl 4-azidopyrrolidine-1,2-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-iodo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester in DMF is added NaN3, the resulting mixture is heated to about 65 centigrade and stirred overnight. The mixture is diluted, extracted and dried. After removal of solvent, the residue is purified to give 4-azido-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl (8).

Workup

  1. temperaturethe resulting mixture is heated to about 65 centigrade
  2. additionThe mixture is diluted
  3. extractionextracted
  4. customdried
  5. customAfter removal of solvent
  6. customthe residue is purified

Sources & evidence

ORD record
ord-46b6fa08834c4401aee658517b96f5ff
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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