6-benzyloxy-3-amino-1,2,3,4-tetrahydro-9H-carbazole → 3-Amino-2,3,4,9-tetrahydro-1H-carbazol-6-ol

HRID 726384Notes

Reaction equation

HRID 726384 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]1[CH2:16][CH2:15][CH:14]([NH2:22])[CH2:13][C:12]2=1)C1C=CC=CC=1.[H][H]>C(O)C.[Ni]>[OH:8][C:9]1[CH:10]=[C:11]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]1[CH2:16][CH2:15][CH:14]([NH2:22])[CH2:13][C:12]2=1

Participants

5

Reactant 2

HCID 226113086-benzyloxy-3-amino-1,2,3,4-tetrahydro-9H-carbazoleHCID 178418361HCID 178418361, compound2×

Product 1

HCID 153417413-Amino-2,3,4,9-tetrahydro-1H-carbazol-6-olYield 56%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of 0.871 gm (2.98 mMol) 6-benzyloxy-3-amino-1,2,3,4-tetrahydro-9H-carbazole in 200 mL ethanol were added about 2.0 gm Raney Nickel and hydrogen introduced to the reaction mixture under balloon pressure. After stirring for 18 hours at room temperature the balloon was refilled with hydrogen and the reaction stirred an additional 3 days at room temperature. The reaction mixture was filtered and the filtrate concentrated under reduced pressure to give a colorless solid. The residual solid was subjected to silica gel chromatography, eluting with 80:15:5 dichloromethane:menthanol:ammonium hydroxide. Fractions shown to contain product were combined and concentrated under reduced pressure to give 0.335 gm (56%) of the title compound.

Workup

  1. additionintroduced to the reaction mixture under balloon pressure
  2. stirringthe reaction stirred an additional 3 days at room temperature
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customto give a colorless solid
  6. washeluting with 80:15:5 dichloromethane
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-afebfb39ca394ce3a8ba64b4edca82a9
Source dataset
uspto-grants-1998_01
Patent number
US05708187

Reaction notes

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