HCID 16117546, compound → HCID 16117683, compound

HRID 1714151Notes

Reaction equation

HRID 1714151 reaction equation
C([N:8]1[CH2:20][C@H:19]2[C@H:11]([C:12](=[O:23])[C:13]3[C:18]2=[CH:17][C:16]([CH3:21])=[CH:15][C:14]=3Br)[CH2:10][CH2:9]1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[CH3:21][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:23])[C@H:11]1[C@@H:19]2[CH2:20][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 1

HCID 16117546HCID 16117546, compound

Product 1

HCID 16117683HCID 16117683, compoundYield 70.7%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of cis-3-benzyl-8-bromo-6-methyl-1,2,3,4,4a,9a-hexahydro-3-aza-fluoren-9-one (50 mg, 0.14 mmol) in MeOH (3.0 mL) was added Pd(OH)2 (10.0 mg, 20 wt %). The reaction mixture was stirred at 20° C. for 15 h under H2 atmosphere, filtered through celite and concentrated in vacuo. The residue was chromatographed in silica gel column (CH2Cl2/MeOH 95/5) to give the title compound (20 mg, 0.099 mmol): MS (ES) 202.2 (M+H).

Workup

  1. filtrationfiltered through celite and
  2. concentrationconcentrated in vacuo
  3. customThe residue was chromatographed in silica gel column (CH2Cl2/MeOH 95/5)

Sources & evidence

ORD record
ord-0c289a0b51314bd2b52d13a98451635a
Source dataset
uspto-grants-2010_09
Patent number
US07795436B2

Reaction notes

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