HCID 67490817, compound → HCID 67490816, compound

HRID 1917394Notes

Reaction equation

HRID 1917394 reaction equation
C(OC([N:11]1[CH2:19][C@@:18]2([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:13]([CH2:14][CH2:15][O:16][CH2:17]2)[CH2:12]1)=O)C1C=CC=CC=1.[H][H]>CO.[C].[Pd]>[C:24]([O:23][C:21]([NH:20][C@:18]12[CH2:19][NH:11][CH2:12][C@H:13]1[CH2:14][CH2:15][O:16][CH2:17]2)=[O:22])([CH3:27])([CH3:25])[CH3:26]

Participants

5

Reactant 2

HCID 67490817HCID 67490817, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67490816HCID 67490816, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

[(1S,6R)-1-tert-Butoxycarbonylamino-3-oxa-8-azabicyclo[4,3,0]nonan-8-yl]carboxylic acid benzyl ester (401 mg, 1.07 mmol) was dissolved in methanol (20 mL). 10% palladium-carbon (50% wet) (200 mg) was added, and the mixture was stirred in a hydrogen atmosphere for 2.5 hours. The catalyst was removed by filtration, and then the filtrate was concentrated under reduced pressure. A 1N sodium hydroxide solution was added, followed by extraction with chloroform. After drying over anhydrous sodium sulfate and filtration, the solvent was evaporated under reduced pressure to give 256 mg of the title compound as a colorless solid.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionA 1N sodium hydroxide solution was added
  4. extractionfollowed by extraction with chloroform
  5. dry with materialAfter drying over anhydrous sodium sulfate and filtration
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6775e86b83ae4ff7815a6d345bbfcb51
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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