HCID 14863941, compound → 1-Tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

HRID 1454266Notes

Reaction equation

HRID 1454266 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([O:10]CC2C=CC=CC=2)[CH2:7][N:6]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:4]>C(OCC)(=O)C>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([OH:10])[CH2:7][N:6]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:4]

Participants

3

Reactant 1

HCID 14863941HCID 14863941, compound

Product 1

HCID 51482991-Tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Benzyloxy-pyrrolidine-1,2-dicarboxylic acid 1-t-butyl ester 2-methyl ester (500 mg, 1.49 mmol) was taken up in ethyl acetate in a Paar vessel. The solution was flushed with argon and Pd/C (200 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 350.98 mg. C11H19NO5 MS m/e=246.2 (M+H).

Workup

  1. customThe solution was flushed with argon and Pd/C (200 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-4d845ae461d2450ea5a2461e3b6b0c2b
Source dataset
uspto-grants-2009_01
Patent number
US07479495B2

Reaction notes

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