tert-butyl 7-(benzyloxy)-9H-carbazol-2-ylcarbamate → tert-butyl 7-hydroxy-9H-carbazol-2-ylcarbamate

HRID 1425564Notes

Reaction equation

HRID 1425564 reaction equation
C([O:8][C:9]1[CH:21]=[C:20]2[C:12]([C:13]3[CH:14]=[CH:15][C:16]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:17][C:18]=3[NH:19]2)=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:21]=[C:20]2[C:12]([C:13]3[CH:14]=[CH:15][C:16]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[CH:17][C:18]=3[NH:19]2)=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 66933893tert-butyl 7-(benzyloxy)-9H-carbazol-2-ylcarbamate

Product 1

HCID 58160239tert-butyl 7-hydroxy-9H-carbazol-2-ylcarbamateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To tert-butyl 7-(benzyloxy)-9H-carbazol-2-ylcarbamate (220 mg, 0.56 mmol) in 50 mL MeOH was added Palladium on activated carbon (80 mg). The mixture was stirred at rt under H2 atmosphere for 3 h. Solid was filtered off and the filtrate was concentrated to afford tert-butyl 7-hydroxy-9H-carbazol-2-ylcarbamate as a brown solid (165 mg, 100%). This material was used directly for the next reaction without purification. MS (ESI) m/z 619 (2M+Na+).

Workup

  1. filtrationSolid was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-fe11093cc7a946ed86281c1bfce5c641
Source dataset
uspto-grants-2015_01
Patent number
US08932557B2

Reaction notes

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