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Sodium Hydroxide → rac-(1R*,2R*,4R*)-2-(2-{[3-(1H-benzoimidazol-2-yl)-propyl]-methyl-amino}-ethyl)-5-thiophen-2-yl-bicyclo[2.2.2]oct-5-en-2-ol

HRID 220298
ノート
印刷プレビュー

反応式

HRID 220298 の反応式
COCCO[AlH2-]OCCOC.[Na+].[NH:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[C:14]1[CH2:22][CH2:23][CH2:24][N:25]([CH3:43])[C:26](=O)[CH2:27][C:28]1([OH:41])[CH2:33][CH:32]2[CH2:34][CH2:35][CH:29]1[CH:30]=[C:31]2[C:36]1[S:37][CH:38]=[CH:39][CH:40]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[NH:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[C:14]1[CH2:22][CH2:23][CH2:24][N:25]([CH3:43])[CH2:26][CH2:27][C:28]1([OH:41])[CH2:33][CH:32]2[CH2:34][CH2:35][CH:29]1[CH:30]=[C:31]2[C:36]1[S:37][CH:38]=[CH:39][CH:40]=1
参加物反応条件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 14798Sodium HydroxideHCID 16684438Red-AlHCID 68412936rac-(1R*,2R*,4R*)-N-[3-(1H-benzoimidazol-2-yl)-propyl]-2-(2-hydroxy-5-thiophen-2-yl-bicyclo[2.2.2]oct-5-en-2-yl)-N-methyl-acetamide

生成物 1

HCID 68415030rac-(1R*,2R*,4R*)-2-(2-{[3-(1H-benzoimidazol-2-yl)-propyl]-methyl-amino}-ethyl)-5-thiophen-2-yl-bicyclo[2.2.2]oct-5-en-2-ol収率 79.7%

試薬・触媒・溶媒 1

HCID 1140
Toluene
溶媒

反応条件

温度
0 °C

実験手順

0.196 mL of a Red-Al solution (65% in toluene) was added dropwise at 0° C. to a solution of 70 mg of rac-(1R*,2R*,4R*)-N-[3-(1H-benzoimidazol-2-yl)-propyl]-2-(2-hydroxy-5-thiophen-2-yl-bicyclo[2.2.2]oct-5-en-2-yl)-N-methyl-acetamide in toluene (0.8 mL). The reaction mixture was stirred for 30 min at 0° C. then the temperature was allowed to increase to rt for 3.5 h. The mixture was carefully poured onto a mixture of 1M-NaOH (6.1 mL) and ice. The mixture was stirred for 5 min until rt and extracted with toluene. The aq. phase was extracted with toluene. The combined toluene phase was washed with 1M-NaOH and brine, dried over anh. Na2SO4 and concentrated in vacuo to yield 54 mg of rac-(1R*,2R*,4R*)-2-(2-{[3-(1H-benzoimidazol-2-yl)-propyl]-methyl-amino}-ethyl)-5-thiophen-2-yl-bicyclo[2.2.2]oct-5-en-2-ol as a colorless solid.

後処理

  1. temperatureto increase to rt for 3.5 h
  2. stirringThe mixture was stirred for 5 min until rt
  3. extractionextracted with toluene
  4. extractionThe aq. phase was extracted with toluene
  5. washThe combined toluene phase was washed with 1M-NaOH and brine
  6. dry with materialdried over anh. Na2SO4
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-5be5f56fe5ce4232ba831ba629018b01
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08202885B2

反応ノート

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