HCID 68936986, compound → HCID 59770430, compound

HRID 2218694Notes

Reaction equation

HRID 2218694 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[C:7](=[CH:16][C:17]3[CH:18]=[C:19]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH:20]=[CH:21][CH:22]=3)[C:6]=2[CH:28]=1>CCOC(C)=O.[Pt]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[CH:7]([CH2:16][C:17]3[CH:18]=[C:19]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH:20]=[CH:21][CH:22]=3)[C:6]=2[CH:28]=1

Participants

4

Reactant 1

HCID 68936986HCID 68936986, compound

Product 1

HCID 59770430HCID 59770430, compoundYield 13.9%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

Dissolve N-[3-(3-chloro-10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-phenyl]-methanesulfonamide (200 mg, 0.49 mmol) in EtOAc (30 mL) and add 5% Pt/C (150 mg). Stir for 18 h under an atmosphere of hydrogen. Add 5% Pt/C (200 mg). Stir for 24 h under an atmosphere of hydrogen. Filter and concentrate to give 140 mg crude product. Purify using reverse-phase UV guided HPLC to give 28 mg viscous tan oil, MS (ES) 410 (M−1). HPLC shows 99% purity.

Workup

  1. stirringStir for 24 h under an atmosphere of hydrogen
  2. filtrationFilter
  3. concentrationconcentrate
  4. customto give 140 mg crude product
  5. customPurify

Sources & evidence

ORD record
ord-034df5f7160240ca8f2a32150bde52d8
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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