HCID 131724993, compound → HCID 131724994, compound

HRID 1071498Notes

Reaction equation

HRID 1071498 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([N:13]=[N+]=[N-])[CH2:10][CH:9]1[C:16]([CH3:24])([CH3:23])[O:17][SiH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([NH2:13])[CH2:10][CH:9]1[C:16]([CH3:24])([CH3:23])[O:17][SiH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 131724993HCID 131724993, compound

Product 1

HCID 131724994HCID 131724994, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The 4-azido-2-(t-butyl-dimethyl-silanyloxymethyl)-pyrrolidine-1-carboxylic acid t-butyl ester (184.83 mg, 0.52 mmol) was taken up in ethyl acetate in a Paar vessel. The solution was flushed with argon and Pd/C (150 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 154.69 mg. C16H34N2O3Si MS m/e=331.2 (M+H).

Workup

  1. customThe solution was flushed with argon and Pd/C (150 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-08979fd22ba94a90940f428a9e9f453b
Source dataset
uspto-grants-2005_06
Patent number
US06906067B2

Reaction notes

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