2-Indanone → 7-Indan-2-yl-9-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene

HRID 40651

Reaktionsgleichung

Reaktionsgleichung von HRID 40651
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=O.[CH:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][C:12]=1[N:21]1[CH2:28][C@H:27]2[NH:29][CH2:30][C@@H:22]1[CH2:23][CH:24]=[CH:25][CH2:26]2.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(OCC)(=O)C.C(O)(=O)C.ClCCCl>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[N:29]1[CH2:30][CH:22]2[N:21]([C:12]3[CH:13]=[CH:14][C:15]4[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH:11]=3)[CH2:28][CH:27]1[CH2:26][CH:25]=[CH:24][CH2:23]2

Komponenten

8

Edukt 4

HCID 119832-IndanoneHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 59686818Z-(1S,6S)-7-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene

Produkt 1

HCID 692343967-Indan-2-yl-9-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of indan-2-one (45 mg, 0.34 mmol), Z-(1S,6S)-7-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene (50 mg, 0.19 mmol), sodium triacetoxyborohydride (45 mg, 0.212 mmol), DCE (20 mL), acetic acid (13 μL) was stirred at room temperature overnight. To the reaction mixture was then added 1N NaOH and ethyl acetate. The organic layer was separated, dried with magnesium sulfate, filtered and the solvent evaporated under reduced pressure to yield a crude solid that was purified with flash chromatography gradient [20% Ethyl acetate/heptane to 100% Ethyl acetate] to yield the title compound as a residue.

Aufarbeitung

  1. customThe organic layer was separated
  2. dry with materialdried with magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent evaporated under reduced pressure
  5. customto yield a crude solid
  6. customthat was purified with flash chromatography gradient [20% Ethyl acetate/heptane to 100% Ethyl acetate]

Quellen und Nachweise

ORD-Eintrag
ord-2a592e7ef57e40439f8f2cd7a6732bb2
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530475B2

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