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

HRID 40651

반응식

HRID 40651 반응식
[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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 111,2-Dichloroethane용매HCID 176Acetic Acid용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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]

출처 및 근거

ORD 기록
ord-2a592e7ef57e40439f8f2cd7a6732bb2
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530475B2

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