Sodium borohydride → 4-(1-Hydroxy-2,2-dimethyl propyl)-2-propyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carbonitrile

HRID 52969ノート

反応式

HRID 52969 の反応式
[BH4-].[Na+].[CH2:3]([C:6]1[N:7]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]3[N:36]([C:37]([C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[N:35]=[N:34][N:33]=3)=[CH:22][CH:21]=2)[C:8]([C:17]#[N:18])=[C:9]([C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])[N:10]=1)[CH2:4][CH3:5]>C(O)C.O1CCCC1>[OH:16][CH:11]([C:9]1[N:10]=[C:6]([CH2:3][CH2:4][CH3:5])[N:7]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]3[N:36]([C:37]([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)([C:50]4[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=4)[C:44]4[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=4)[N:35]=[N:34][N:33]=3)=[CH:24][CH:25]=2)[C:8]=1[C:17]#[N:18])[C:12]([CH3:15])([CH3:13])[CH3:14]

参加物

5

反応物 2

HCID 4311764Sodium borohydrideHCID 217408232-Propyl-4-pivaloyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carbonitrile

生成物 1

HCID 190362484-(1-Hydroxy-2,2-dimethyl propyl)-2-propyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carbonitrile収率 96.2%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 108 mg of sodium borohydride in 20 ml of ethanol was added to a solution of 2.00 g of 2-propyl-4-pivaloyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carbonitrile [prepared as described in step (a) above] in 40 ml of tetrahydrofuran, and the mixture was stirred at room temperature for 2.5 hours. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and the residue was dissolved in a mixture of ethyl acetate and water. The ethyl acetate layer was separated, washed with water, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The syrupy residue was crystallized in a 1:4 by volume mixture of ethyl acetate and hexane, to give 1.93 g of the title compound as crystals, melting at 115°-117° C.

後処理

  1. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  2. dissolutionthe residue was dissolved in a mixture of ethyl acetate and water
  3. customThe ethyl acetate layer was separated
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customThe syrupy residue was crystallized in a 1:4 by volume mixture of ethyl acetate and hexane

出典と根拠

ORDレコード
ord-4d5d9b06a7144ca79a676f564c8b5a52
出典データセット
uspto-grants-1997_04
特許番号
US05616599

反応ノート

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