Acetic Acid → cis-8-Methyl-6-phenyl-2,3,4,4a,9,9a-hexahydro-1H-3-aza-fluorene

HRID 1714145Notes

Reaction equation

HRID 1714145 reaction equation
C([N:8]1[CH2:20][C@H:19]2[C@H:11]([CH2:12][C:13]3[C:18]2=[CH:17][C:16]([C:21]2[CH:26]=[CH:25][C:24](Cl)=[CH:23][C:22]=2Cl)=[CH:15][C:14]=3[CH3:29])[CH2:10][CH2:9]1)C1C=CC=CC=1.C(O)(=O)C>CO.[OH-].[OH-].[Pd+2]>[CH3:29][C:14]1[CH:15]=[C:16]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:17]=[C:18]2[C:13]=1[CH2:12][C@H:11]1[C@@H:19]2[CH2:20][NH:8][CH2:9][CH2:10]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 16117676cis-3-Benzyl-6-(2,4-dichloro-phenyl)-8-methyl-2,3,4,4a,9,9a-hexahydro-1H-3-aza-fluorene

Product 1

HCID 16117678cis-8-Methyl-6-phenyl-2,3,4,4a,9,9a-hexahydro-1H-3-aza-fluoreneYield 42%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of cis-3-benzyl-6-(2,4-dichloro-phenyl)-8-methyl-2,3,4,4a,9,9a-hexahydro-1H-3-aza-fluorene (85 mg, 0.20 mmol) in MeOH (3.0 mL) was added Pd(OH)2 (17 mg, 20 wt %) and catalytic amount of acetic acid. The reaction mixture was stirred at 20° C. for 3 days under H2 atmosphere, filtered through celite and concentrated in vacuo. The residue was chromatographed in silica gel column (Hex/EtOAc 1/1) to give the title compound (22 mg, 0.084 mmol): MS (ES) 264.2 (M+H).

Workup

  1. filtrationfiltered through celite and
  2. concentrationconcentrated in vacuo
  3. customThe residue was chromatographed in silica gel column (Hex/EtOAc 1/1)

Sources & evidence

ORD record
ord-4e2bfc353dce4c59abedefe5727cba99
Source dataset
uspto-grants-2010_09
Patent number
US07795436B2

Reaction notes

Loading…