Acetic Acid → HCID 16117680, compound

HRID 1714148Notes

Reaction equation

HRID 1714148 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]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:22]=2[Cl:31])=[CH:15][C:14]=3[CH3:32])[CH2:10][CH2:9]1)C1C=CC=CC=1.C(O)(=O)C>CO.[OH-].[OH-].[Pd+2]>[Cl:31][C:22]1[CH:23]=[C:24]([C:27]([F:30])([F:28])[F:29])[CH:25]=[CH:26][C:21]=1[C:16]1[CH:17]=[C:18]2[C:13](=[C:14]([CH3:32])[CH:15]=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 16117677HCID 16117677, compound

Product 1

HCID 16117680HCID 16117680, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of cis-3-benzyl-6-(2-chloro-4-trifluoromethyl-phenyl)-8-methyl-2,3,4,4a,9,9a-hexahydro-1H-3-aza-fluorene (25 mg, 0.055 mmol) in MeOH (1.5 mL) was added Pd(OH)2 (5.0 mg, 20 wt %) and catalytic amount of acetic acid. The reaction mixture was stirred at 20° C. for 10 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 (16 mg, 0.044 mmol): MS (ES) 366.1 (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-3ce789127e894f99a111ed2fb25cfe50
Source dataset
uspto-grants-2010_09
Patent number
US07795436B2

Reaction notes

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