Sodium Azide → (2S,4R)-4-Azido-1,2-pyrrolidinedicarboxylic Acid 1-(1,1-Dimethylethyl) 2-Methyl Ester

HRID 490659Notes

Reaction equation

HRID 490659 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.O>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H: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

5

Reactant 2

HCID 33557Sodium AzideHCID 675472144-Iodo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Product 1

HCID 11369242(2S,4R)-4-Azido-1,2-pyrrolidinedicarboxylic Acid 1-(1,1-Dimethylethyl) 2-Methyl EsterYield 91.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-iodo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (20 mmol, 1 equiv) in DMF was added NaN3 (2.5 equiv, 50 mmol), the resulting mixture was heated to 65 centigrade and stirred overnight. The mixture was diluted with water, extracted with AcOEt and dried over Na2SO4. After removal of solvent, the residue was purified by chromatography on silica gel to give title product (4.94 g) as colorless oil in 90% yield. MS m/e=271.5 [M+H]+.

Workup

  1. temperaturethe resulting mixture was heated to 65 centigrade
  2. extractionextracted with AcOEt
  3. dry with materialdried over Na2SO4
  4. customAfter removal of solvent
  5. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-5f585658e99244eea77e08ad85768d79
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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