Red-Al → HCID 66877393、化合物

HRID 453713ノート

反応式

HRID 453713 の反応式
[CH3:1][O:2][C:3]1[C:11]2[N:10]=[C:9]([CH2:12][CH2:13][CH2:14][N:15]([CH3:34])[C:16](=O)[CH2:17][C:18]3([OH:32])[CH2:23][CH:22]4[CH2:24][CH2:25][CH:19]3[CH:20]=[C:21]4[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[NH:8][C:7]=2[C:6]([O:35][CH3:36])=[CH:5][CH:4]=1.COCCO[AlH2-]OCCOC.[Na+]>C1(C)C=CC=CC=1>[CH3:36][O:35][C:6]1[C:7]2[N:8]=[C:9]([CH2:12][CH2:13][CH2:14][N:15]([CH3:34])[CH2:16][CH2:17][C:18]3([OH:32])[CH2:23][CH:22]4[CH2:24][CH2:25][CH:19]3[CH:20]=[C:21]4[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[NH:10][C:11]=2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

参加物

4

反応物 2

HCID 16684438Red-AlHCID 77305456HCID 77305456、化合物

生成物 1

HCID 66877393HCID 66877393、化合物収率 76.4%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
0 °C

実験手順

To a solution of 310 mg of rac-(1R*,2R*,4R*)-N-[3-(4,7-dimethoxy-1H-benzoimidazol-2-yl)-propyl]-2-(2-hydroxy-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl)-N-methyl-acetamide in 8 mL toluene were added dropwise 0.77 mL of a Red-Al solution (65% in toluene) at 0° C. After stirring for 10 min at 0° C., the cooling bath was removed and stirring was continued for 3 h at rt. The reaction mixture was then carefully poured onto a mixture of 1M NaOH/ice and stirred for 10 min. The aq. phase was extracted with toluene, the combined organic phases were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification by CC using EtOAc-MeOH (2:1) yielded 230 mg of rac-(1R*,2R*,4R*)-2-(2-{[3-(4,7-dimethoxy-1H-benzoimidazol-2-yl)-propyl]-methyl-amino}-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-ol as white foam.

後処理

  1. customthe cooling bath was removed
  2. stirringstirring
  3. waitwas continued for 3 h at rt
  4. additionThe reaction mixture was then carefully poured onto a mixture of 1M NaOH/ice
  5. stirringstirred for 10 min
  6. extractionThe aq. phase was extracted with toluene
  7. washthe combined organic phases were washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customPurification by CC

出典と根拠

ORDレコード
ord-fadf4de03ef04b21b87964155a14ce63
出典データセット
uspto-grants-2013_07
特許番号
US08492555B2

反応ノート

読み込み中…