Lithium aluminum hydride → (2-Amino-1-cyclohexyl-1H-benzimidazol-5-yl)methanol

HRID 2068286ノート

反応式

HRID 2068286 の反応式
[NH2:1][C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[C:5]2[CH:13]=[CH:14][C:15]([C:17](OCC)=[O:18])=[CH:16][C:4]=2[N:3]=1.[AlH4-].[Li+]>O1CCCC1>[NH2:1][C:2]1[N:6]([CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[C:5]2[CH:13]=[CH:14][C:15]([CH2:17][OH:18])=[CH:16][C:4]=2[N:3]=1

参加物

4

反応物 2

HCID 28112Lithium aluminum hydrideHCID 67254051Ethyl 2-amino-1-cyclohexyl-1H-benzo[d]imidazole-5-carboxylate

生成物 1

HCID 67252967(2-Amino-1-cyclohexyl-1H-benzimidazol-5-yl)methanol収率 91.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

In a 20 mL vial, ethyl 2-amino-1-cyclohexyl-1H-benzo[d]imidazole-5-carboxylate (101.5 mg, 0.0003532 mol) was dissoled in tetrahydrofuran (2 mL, 0.02 mol). While stirring under nitrogen, a solution of 1.0 M of lithium tetrahydroaluminate in tetrahydrofuran (1.0 mL) was added dropwise via a syringe to the reaction mixture. An initial reddish color occured followed by the reaction mixture becoming straw colored and a precipitate formed. After 1 hour the reaction was quenched by the dropwise addition of saturated ammonium chloride (1 mL). The mixture was extracted with ethyl acetate three times, the combined organic phases dried over sodium sulfate and concentrated to give the title compound (79.4 mg) as an off white solid.

後処理

  1. customa precipitate formed
  2. customAfter 1 hour the reaction was quenched by the dropwise addition of saturated ammonium chloride (1 mL)
  3. extractionThe mixture was extracted with ethyl acetate three times
  4. dry with materialthe combined organic phases dried over sodium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-da6c08cc747247829872a0732a547e8c
出典データセット
uspto-grants-2012_10
特許番号
US08293923B2

反応ノート

読み込み中…