(4aS,8aS)-1-benzyl-4-(phenylamino)octahydroquinolin-4a(2H)-ol → HCID 68154084, compound

HRID 73614Notes

Reaction equation

HRID 73614 reaction equation
C([N:8]1[C@@H:17]2[C@:12]([OH:18])([CH2:13][CH2:14][CH2:15][CH2:16]2)[CH:11]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1>CO.[Pd]>[C:20]1([NH:19][CH:11]2[C@:12]3([OH:18])[C@H:17]([CH2:16][CH2:15][CH2:14][CH2:13]3)[NH:8][CH2:9][CH2:10]2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 1

HCID 52911548(4aS,8aS)-1-benzyl-4-(phenylamino)octahydroquinolin-4a(2H)-ol

Product 1

HCID 68154084HCID 68154084, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of (4aS,8aS)-1-benzyl-4-(phenylamino)octahydroquinolin-4a(2H)-ol (0.280 g, 0.832 mmol) in MeOH (5 mL) was added NH4COOH (0.840 g, 13.3 mmol) and 10% Pd/C (0.280 g). The resulting mixture was heated at 60° C. for several hours. The reaction was cooled to rt, filtered through a syringe filter, washed with EtOH, and concentrated to give the title compound. LRMS M+H calc'd: 247.34. found 247.34

Workup

  1. temperatureThe reaction was cooled to rt
  2. filtrationfiltered through a syringe
  3. filtrationfilter
  4. washwashed with EtOH
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4f198c0a3a474dfe812baf3eda919d30
Source dataset
uspto-grants-2014_09
Patent number
US08829196B2

Reaction notes

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