HCID 131724991, compound → HCID 131724990, compound

HRID 1454255Notes

Reaction equation

HRID 1454255 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13]CC2C=CC=CC=2)[CH2:10][CH:9]1[C:21]([CH3:29])([CH3:28])[O:22][SiH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[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]([OH:13])[CH2:10][CH:9]1[C:21]([CH3:29])([CH3:28])[O:22][SiH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 131724991HCID 131724991, compound

Product 1

HCID 131724990HCID 131724990, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The 4-benzyloxy-2-(t-butyl-dimethyl-silanyloxymethyl)-pyrrolidine-1-carboxylic acid t-butyl ester (267.49 mg, 0.63 mmol) was taken up in ethyl acetate in a Paar vessel. The solution was flushed with argon and Pd/C (100 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 192.15 mg. C16H33NO4Si ms m/e=3.32.2 (M+H).

Workup

  1. customThe solution was flushed with argon and Pd/C (100 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-e8262a1cef8d42e796b824ca08f8db64
Source dataset
uspto-grants-2009_01
Patent number
US07479495B2

Reaction notes

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