HCID 68079399, compound → HCID 66850120, compound

HRID 1528293Notes

Reaction equation

HRID 1528293 reaction equation
C([N:8]1[C@@H:17]2[C@@H:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)[N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>[OH-].[OH-].[Pd+2].CCO>[N:11]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@H:12]2[C@H:17]([CH2:16][CH2:15][CH2:14][CH2:13]2)[NH:8][CH2:9][CH2:10]1

Participants

5

Reactant 2

HCID 68079399HCID 68079399, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66850120HCID 66850120, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Pearlman's catalyst (0.24 g) was added to an EtOH (25 ml) solution of (4aS,8aR) -tert-butyl 4-benzyldecahydroquinoxaline-1-carboxylate (2.4 g, 7.26 mmol). This suspension was stirred at room temperature for 1 hour in a hydrogen atmosphere. The catalyst was filtered through celite, and the residue was washed with EtOH. Then, the filtrate was concentrated under reduced pressure to obtain (4aS,8aR)-tert-butyl decahydroquinoxaline-1-carboxylate (1.67 g, yield: 96%) in a colorless oil form.

Workup

  1. filtrationThe catalyst was filtered through celite
  2. washthe residue was washed with EtOH
  3. concentrationThen, the filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-540855a0120c4351a54dd5ae22d9609f
Source dataset
uspto-grants-2015_07
Patent number
US09090572B2

Reaction notes

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