(E)-5-(4-(2-(5-ethylpyridin-2-yl)ethoxy)benzylidene)thiazolidine-2,4-dione → Pioglitazone, (R)-

HRID 882706

反応式

HRID 882706 の反応式
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15](/[CH:18]=[C:19]3\[C:20](=[O:25])[NH:21][C:22](=[O:24])[S:23]\3)=[CH:14][CH:13]=2)=[N:7][CH:8]=1)[CH3:2]>C(Cl)Cl.CO.CCO>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C@H:19]3[S:23][C:22](=[O:24])[NH:21][C:20]3=[O:25])=[CH:14][CH:13]=2)=[N:7][CH:8]=1)[CH3:2]

参加物

5

反応物 1

HCID 14211277(E)-5-(4-(2-(5-ethylpyridin-2-yl)ethoxy)benzylidene)thiazolidine-2,4-dione

生成物 1

HCID 29010894Pioglitazone, (R)-

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

A stock solution of the Rh(COD)2BF4 (10.6 mg, 26.1 μmol) in DCM (9.5 mL) was made in a glove box. Ligand SL-WO03-2 ((S)-1-[(S)-2-(2i -diphenylphosphinophenyl)ferrocenyl]ethyl-dicyclohexyl phosphine) (8.4 mg, 12.5 μmol), was weighed into a vial and 500 μL of the Rh(COD)2BF4 stock solution was added. A solution of 5-[1-{4-[2-(5-ethyl-pyridin-2-yl)-ethoxy]-phenyl}-meth-(E)-ylidene]-thiazolidine-2,4-dione (4.5 mL of a stock solution containing 78.2 mg in 35 mL MeOH) was added to the reaction vial containing the catalyst solution. The vial was purged with N2 (5×) and H2 (5×) and finally charged with 25 bar of H2. After 18 h the H2 was released and the reaction vial was purged with N2 (3×). A sample of the reaction vial was taken and diluted with an equal volume of EtOH containing 1% formic acid. e.e. (Method 4) 75%, Rt 36.11 min, conversion 50%.

後処理

  1. additionwas added
  2. additionwas added to the reaction
  3. additionvial containing the catalyst solution
  4. customThe vial was purged with N2 (5×) and H2 (5×)
  5. additionfinally charged with 25 bar of H2
  6. customthe reaction
  7. customvial was purged with N2 (3×)
  8. customA sample of the reaction

出典と根拠

ORDレコード
ord-bce85533d58a4772baa668753a77e8e5
出典データセット
uspto-grants-2012_08
特許番号
US08236786B2

関連ノート

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