HCID 68816170, compound → HCID 68815003, compound

HRID 732382Notes

Reaction equation

HRID 732382 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11](=[CH:13][C:14]([O:16][CH3:17])=[O:15])[CH2:10][C@@H:9]1[C@H:18]1[O:22][C:21]([CH3:24])([CH3:23])[N:20]([C:25](=[O:27])[CH3:26])[C@H:19]1[CH2:28][C:29]1[CH:34]=[C:33]([F:35])[CH:32]=[C:31]([F:36])[CH:30]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH2:10][C@@H:9]1[C@H:18]1[O:22][C:21]([CH3:24])([CH3:23])[N:20]([C:25](=[O:27])[CH3:26])[C@H:19]1[CH2:28][C:29]1[CH:34]=[C:33]([F:35])[CH:32]=[C:31]([F:36])[CH:30]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 68816170HCID 68816170, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68815003HCID 68815003, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Combine (R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-[1-methoxycarbonyl-methylidene]-pyrrolidine-1-carboxylic acid tert-butyl ester (as mixture of isomers Z/E) (0.010 g, 0.02 mmol), 10% palladium on carbon (4 mg) and methanol (2 mL) and stir for 3 hours under 1 atmosphere of hydrogen. Add filter agent, filter and concentrate under reduced pressure to provide the desired compound as a mixture of cis and trans isomers, (0.01 g, 98%).

Workup

  1. additionAdd
  2. filtrationfilter agent
  3. filtrationfilter
  4. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-23da8d9991eb4cac8947664c0af1d3f4
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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