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

HRID 40651

反応式

HRID 40651 の反応式
[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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 111,2-Dichloroethane溶媒HCID 176Acetic Acid溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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]

出典と根拠

ORDレコード
ord-2a592e7ef57e40439f8f2cd7a6732bb2
出典データセット
uspto-grants-2013_09
特許番号
US08530475B2

関連ノート

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