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Acetone → 1-[(2'-t-Butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-(1-hydroxyethyl)imidazole-5-carbonitrile

HRID 52920
ノート
印刷プレビュー

反応式

HRID 52920 の反応式
[BH4-].[Na+].[C:3]([C:6]1[N:7]=[C:8]([CH2:33][CH2:34][CH2:35][CH3:36])[N:9]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[CH:16][CH:15]=2)[C:10]=1[C:11]#[N:12])(=[O:5])[CH3:4].CC(C)=O>C(O)C>[C:29]([O:28][C:26]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:9]2[C:10]([C:11]#[N:12])=[C:6]([CH:3]([OH:5])[CH3:4])[N:7]=[C:8]2[CH2:33][CH2:34][CH2:35][CH3:36])=[CH:15][CH:16]=1)=[O:27])([CH3:32])([CH3:31])[CH3:30]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 180AcetoneHCID 4311764Sodium borohydride2 回HCID 190361124-Acetyl-1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-5-cyanoimidazole

生成物 1

HCID 190362351-[(2'-t-Butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-(1-hydroxyethyl)imidazole-5-carbonitrile収率 99.6%

試薬・触媒・溶媒 1

HCID 702Ethanol
溶媒

実験手順

0.098 g of sodium borohydride was added to a solution of 1.18 g of 4-acetyl-1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butylimidazole-5-carbonitrile [prepared as described in step (a) above] in 30 ml of ethanol, and the resulting mixture was stirred at room temperature for 1 hour. The excess sodium borohydride was decomposed by adding acetone, and then the reaction mixture was concentrated by evaporation under reduced pressure. The residue was diluted with an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was dried and concentrated by evaporation under reduced pressure. The oily residue was purified by column chromatography through silica gel, using a 3:2 by volume mixture of ethyl acetate and hexane as the eluent, to afford 1.18 g of the title compound as a viscous oil.

後処理

  1. concentrationthe reaction mixture was concentrated by evaporation under reduced pressure
  2. additionThe residue was diluted with an aqueous solution of sodium chloride
  3. extractionextracted with ethyl acetate
  4. customThe extract was dried
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customThe oily residue was purified by column chromatography through silica gel
  7. additionby volume mixture of ethyl acetate and hexane as the eluent

出典と根拠

ORDレコード
ord-03392fbbd4a347f9bfe4f71b3badbc66
出典データセット
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05616599

反応ノート

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