HCID 67491058, compound → HCID 131731119, compound

HRID 1917438Notes

Reaction equation

HRID 1917438 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][C:8]12[CH2:15][O:14][C@H:13]3[CH2:16][C:12]13[CH2:11][N:10]([C@@H](C1C=CC=CC=1)C)[CH2:9]2)([CH3:4])([CH3:3])[CH3:2]>O1CCOCC1.[OH-].[Pd+2].[OH-]>[C:1]([O:5][C:6](=[O:25])[NH:7][C:8]12[CH2:15][O:14][C@H:13]3[CH2:16][C:12]13[CH2:11][NH:10][CH2:9]2)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 67491058HCID 67491058, compound

Product 1

HCID 131731119HCID 131731119, compoundYield 83.8%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 312751,4-DioxaneSolvent

Procedure

An [(S)-5-[(R)-1-Phenylethyl]tetrahydro-2-oxa-5-azacyclopropa[c]pentalen-3a-yl]carbamic acid tert-butyl ester (480 mg, 1.39 mmol) was dissolved in dioxane (10 ml) and 20% palladium hydroxide catalyst (20 wt. % Pd on carbon, wet; cat.) was added. The mixture was vigorously stirred under a hydrogen atmosphere at room temperature for 3 days. After removing the catalyst by filtration, the filtrate was concentrated under reduced pressure. The residue was taken up in dichloromethane, and washed with 1N aq. NaOH and brine. The organic layer was dried over anhydrous sodium sulfate and the solvent removed in vacuo to give the crude title compound as a white solid (280 mg).

Workup

  1. customAfter removing the catalyst
  2. filtrationby filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. washwashed with 1N aq. NaOH and brine
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-aa62f8b133b54c169b93592ab8010df1
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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