4-Benzyloxy-2-methyl-pyrrolidine-1-carboxylic acid t-butyl ester → tert-Butyl 4-hydroxy-2-methylpyrrolidine-1-carboxylate

HRID 1071501Notes

Reaction equation

HRID 1071501 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[CH3:21])=[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[CH3:21])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 685666364-Benzyloxy-2-methyl-pyrrolidine-1-carboxylic acid t-butyl ester

Product 1

HCID 14117009tert-Butyl 4-hydroxy-2-methylpyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The 4-benzyloxy-2-methyl-pyrrolidine-1-carboxylic acid t-butyl ester (168.57 mg, 0.58 mmol) was taken up in ethyl acetate in a Paar vessel. The solution was flushed with argon and Pd/C (100.00 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 110.89 mg. C10H19NO3 MS m/e=202.1 (M+H).

Workup

  1. customThe solution was flushed with argon and Pd/C (100.00 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-ed56fc06da5843f09cb7e4989e006d83
Source dataset
uspto-grants-2005_06
Patent number
US06906067B2

Reaction notes

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