HCID 68770982, compound → HCID 59556944, compound

HRID 1173597Notes

Reaction equation

HRID 1173597 reaction equation
C(OC([NH:11][C@@H:12]([CH3:30])[CH:13]([O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[C:14]([CH3:21])([CH3:20])[C:15](OCC)=[O:16])=O)C1C=CC=CC=1>CO.[C].[Pd]>[Si:23]([O:22][C@@H:13]1[C@H:12]([CH3:30])[NH:11][C:15](=[O:16])[C:14]1([CH3:21])[CH3:20])([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24].[Si:23]([O:22][C@H:13]1[C@H:12]([CH3:30])[NH:11][C:15](=[O:16])[C:14]1([CH3:21])[CH3:20])([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]

Participants

5

Reactant 1

HCID 68770982HCID 68770982, compound

Product 2

HCID 59556936HCID 59556936, compoundYield 30.1%HCID 59556944HCID 59556944, compoundYield 53.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of ethyl(4S)-4-{[(benzyloxy)carbonyl]amino}-3-(tert-butyldimethylsilyloxy)-2,2-dimethylpentanoate (0.916 g) in methanol (20 mL) was added 10% palladium carbon (containing 50% water, 89 mg), and the mixture was stirred at room temperature for 16 hr under a hydrogen atmosphere and filtered. The filtrate was concentrated under reduced pressure, and the residue was dissolved in THF (15 mL). Diisopropylethylamine (1.5 mL) was added, and the mixture was fluxed for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=30/1→1/3) to give the title compound (yield: 161.8 mg, yield: 30.1%) and (4R,5S)-4-(tert-butyldimethylsilyloxy)-3,3,5-trimethylpyrrolidin-2-one (yield: 289 mg, yield: 53.7%), each as a colorless solid.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in THF (15 mL)
  4. additionDiisopropylethylamine (1.5 mL) was added
  5. waitthe mixture was fluxed for 3 hr
  6. additionWater was added to the reaction mixture
  7. extractionthe mixture was extracted with ethyl acetate
  8. dry with materialThe extract was dried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=30/1→1/3)

Sources & evidence

ORD record
ord-5ff7418704214a83943021076f289170
Source dataset
uspto-grants-2010_11
Patent number
US07834051B2

Reaction notes

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