HCID 178451674, Verbindung → HCID 178451671, Verbindung

HRID 1412925Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1412925
[Cl:1][C:2]1[CH:7]=[C:6]2[CH2:8][O:9][C:10]3[CH:34]=[C:33]4[C:13]([CH2:14][CH2:15][C:16]5[N:20]=[C:19]([CH:21]6[CH2:25][CH2:24][CH2:23][N:22]6[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[NH:18][C:17]=54)=[CH:12][C:11]=3[C:5]2=[CH:4][CH:3]=1>ClCCl.C(OCC)(=O)C.[O-2].[Mn+4].[O-2]>[Cl:1][C:2]1[CH:7]=[C:6]2[CH2:8][O:9][C:10]3[CH:34]=[C:33]4[C:13]([CH:14]=[CH:15][C:16]5[N:20]=[C:19]([CH:21]6[CH2:25][CH2:24][CH2:23][N:22]6[C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])[NH:18][C:17]=54)=[CH:12][C:11]=3[C:5]2=[CH:4][CH:3]=1

Komponenten

5

Edukt 1

HCID 178451674HCID 178451674, Verbindung

Produkt 1

HCID 178451671HCID 178451671, VerbindungAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 2-(9-chloro-1,4,5,11-tetrahydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-2-yl)pyrrolidine-1-carboxylate (1.9 g, 3.96 mmol) in dichloromethane (35 mL) was added manganese(IV) oxide (17 g, 198 mmol). The reaction mixture was stirred at room temperature for 18 hours, diluted with ethyl acetate. The organics were washed with water and brine, dried (Na2SO4), and concentrated. The crude residue was purified by flash chromatography to yield tert-butyl 2-(9-chloro-1,11-dihydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-2-yl)pyrrolidine-1-carboxylate (1.52 g, 81%). LCMS-ESI+: calculated for C27H26ClN3O3: 475.9; observed [M+1]+: 476.45.

Aufarbeitung

  1. washThe organics were washed with water and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0a330de0d3e9437fa3e1c04c06079865
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921341B2

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