HCID 10791798, compound → HCID 10839455, compound

HRID 1953048Notes

Reaction equation

HRID 1953048 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH:11]=[C:10]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:24][CH:23]=2)[C:9]1=[O:36])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.CCCCCC.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH2:11][C@@H:10]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[CH:24][CH:23]=2)[C:9]1=[O:36])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 1

HCID 10791798HCID 10791798, compound

Product 1

HCID 10839455HCID 10839455, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (5R)-3-(4-benzyloxyphenyl)-5-(tert-butyldimethylsilanyloxymethyl)-2-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester (2.0 g, 3.92 mmol) in ethyl acetate (40 mL) and hexane (40 mL) was treated with 20% palladium hydroxide on carbon (200 mg) and hydrogenated in a Parr™ shaker at 3 atmospheres pressure for 2 hours. The catalyst was removed by filtration and the solvent was evaporated to provide the title compound as a yellow oil (2.0 g, 100%).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c078ccac967d4667aa646943a542ca2b
Source dataset
uspto-grants-2000_09
Patent number
US06114361

Reaction notes

Loading…