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

HRID 2068286노트

반응식

HRID 2068286 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-da6c08cc747247829872a0732a547e8c
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08293923B2

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