HCID 59398345、化合物 → (5-benzyloxy-2-oxoquinolin-1(2H)-yl)acetaldehyde

HRID 39894ノート

反応式

HRID 39894 の反応式
[O:1]1CCO[CH:2]1[CH2:6][N:7]1[C:16]2[C:11](=[C:12]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]1=[O:25]>FC(F)(F)C(O)=O>[CH2:18]([O:17][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:11]=1[CH:10]=[CH:9][C:8](=[O:25])[N:7]2[CH2:6][CH:2]=[O:1])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

参加物

3

反応物 1

HCID 59398345HCID 59398345、化合物

生成物 1

HCID 86669947(5-benzyloxy-2-oxoquinolin-1(2H)-yl)acetaldehyde

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

750 mg of 1-(1,3-dioxolan-2-ylmethyl)-5-benzyloxyquinolin-2(1H)-one was dissolved in 3 mL of 90% aqueous trifluoroacetic acid solution, and stirred at room temperature for 3 days. The solvent was removed under reduced pressure, and after it was alkalized by aqueous saturated sodium hydrogen carbonate solution, it was extracted with ethyl acetate. The organic layer was washed sequentially with water and aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to give (5-benzyloxy-2-oxoquinolin-1(2H)-yl)acetaldehyde as a pale yellow solid. (2) To 25 mL of a chloroform solution containing (5-benzyloxy-2-oxoquinolin-1(2H)-yl)acetaldehyde and 877 mg of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(piperidin-4-yl)carbamate, 144 μL of acetic acid was added, and stirred at room temperature for 1 hour. To the reaction mixture, 811 mg of sodium triacetoxyborohydride was added, and stirred for 1.5 hours. Aqueous saturated sodium hydrogen carbonate solution was added, the organic layer was separated. The organic layer was washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [Silica Gel; Kanto Chemical Co., Inc., Silica Gel 60, eluent; chloroform:methanol=100:1], to give 592 mg of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl) (1-(2-(5-benzyloxy-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate as a pale brown foam.

後処理

  1. customThe solvent was removed under reduced pressure
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed sequentially with water and aqueous saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-3ea903faea8747fb87f433fb422cf31b
出典データセット
uspto-grants-2013_09
特許番号
US08524738B2

反応ノート

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