HCID 67491079, compound → HCID 67490928, compound

HRID 1917436Notes

Reaction equation

HRID 1917436 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][C@@:8]12[CH2:23][O:22][CH2:21][CH:9]1[CH2:10][N:11]([C@@H](C1C=CC=CC=1)C)[CH2:12]2)([CH3:4])([CH3:3])[CH3:2]>O1CCOCC1.[OH-].[Pd+2].[OH-]>[C:1]([O:5][C:6](=[O:24])[NH:7][C@@:8]12[CH2:23][O:22][CH2:21][CH:9]1[CH2:10][NH:11][CH2:12]2)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 67491079HCID 67491079, compound

Product 1

HCID 67490928HCID 67490928, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

[(3aS)-5-[(R)-1-Phenylethyl]tetrahydrofuro[3,4-c]pyrrol-3a-yl]carbamic acid tert-butyl ester (355 mg, 1.06 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 40° C. for 24 h. 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 (243 mg) as a colorless syrup.

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-57459af4eebb4621846e721072b94b21
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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