1-Tert-butyl 2-methyl 4-azidopyrrolidine-1,2-dicarboxylate → 1-Tert-butyl 2-methyl 4-aminopyrrolidine-1,2-dicarboxylate

HRID 1071509Notes

Reaction equation

HRID 1071509 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([N:10]=[N+]=[N-])[CH2:7][N:6]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:4]>C(OCC)(=O)C>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([NH2:10])[CH2:7][N:6]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:4]

Participants

3

Reactant 1

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

Product 1

HCID 49130641-Tert-butyl 2-methyl 4-aminopyrrolidine-1,2-dicarboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Azido-pyrrolidine-1,2-dicarboxylic acid 1-t-butyl ester 2-methyl ester (303.10 mg, 1.12 mmol) was taken up in ethyl acetate in a Paar vessel. The solution was flushed with argon and Pd/C (400.00 mg) was added to the vessel. The argon atmosphere was replaced by hydrogen at 50 psi. The vessel was shaken for 12 h. The hydrogen atmosphere was replaced by argon and the solution was filtered through a celite pad. The pad was washed twice with ethyl acetate. The solvent was removed under reduced pressure. The product was used without further purification. Yield 262.66 mg. C11H20N2O4 MS m/e=244.2 (M+).

Workup

  1. customThe solution was flushed with argon and Pd/C (400.00 mg)
  2. additionwas added to the vessel
  3. filtrationthe solution was filtered through a celite pad
  4. washThe pad was washed twice with ethyl acetate
  5. customThe solvent was removed under reduced pressure
  6. customThe product was used without further purification

Sources & evidence

ORD record
ord-603d5dd924ed48a3b69001a80a0ce95a
Source dataset
uspto-grants-2005_06
Patent number
US06906067B2

Reaction notes

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