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Triethylamine → rac-2,2-dimethyl propionic acid (1R*,2R*,4R*)-2-(2-{[3-(4-methoxy-1H-benzoimidazol-2-yl)-propyl]-methyl-amino}-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl ester

HRID 220302
ノート
印刷プレビュー

反応式

HRID 220302 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]([CH3:33])[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:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[NH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.CCN(CC)CC.[C:41](Cl)(=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43]>C(Cl)Cl.C1COCC1.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3]1[C:11]2[N:10]=[C:9]([CH2:12][CH2:13][CH2:14][N:15]([CH3:33])[CH2:16][CH2:17][C@:18]3([O:32][C:41](=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43])[CH2:23][C@H:22]4[CH2:24][CH2:25][C@@H:19]3[CH:20]=[C:21]4[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[NH:8][C:7]=2[CH:6]=[CH:5][CH:4]=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

7

反応物 3

HCID 8471Triethylamine2 回HCID 62493Pivaloyl chloride2 回HCID 68412969rac-(1R*,2R*,4R*)-2-(2-{[3-(4-methoxy-1H-benzoimidazol-2-yl)-propyl]-methyl-amino}-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-ol

生成物 1

HCID 91398129rac-2,2-dimethyl propionic acid (1R*,2R*,4R*)-2-(2-{[3-(4-methoxy-1H-benzoimidazol-2-yl)-propyl]-methyl-amino}-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl ester

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒
HCID 6344Dichloromethane溶媒
HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of 150 mg of rac-(1R*,2R*,4R*)-2-(2-{[3-(4-methoxy-1H-benzoimidazol-2-yl)-propyl]-methyl-amino}-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-ol in 2 mL DCM and 2 mL THF were added 0.21 mL of NEt3 and 41 mg of DMAP. The reaction mixture was cooled to 0° C., 0.17 mL of pivaloyl chloride were added and it was then stirred at 65° C. for 24 h. During the next 4 days further 0.52 mL of NEt3 and 0.41 mL of pivaloyl chloride were added in small aliquots. The reaction was quenched with sat. aq. NaHCO3, extracted with DCM, dried and concentrated in vacuo. Purification by CC using DCM-MeOH (10:1) yielded 40 mg of rac-2,2-dimethyl propionic acid (1R*,2R*,4R*)-2-(2-{[3-(4-methoxy-1H-benzoimidazol-2-yl)-propyl]-methyl-amino}-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl ester as brownish foam.

後処理

  1. customThe reaction was quenched with sat. aq. NaHCO3
  2. extractionextracted with DCM
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customPurification by CC

出典と根拠

ORDレコード
ord-369268f360f44479a2cf80dfdfaf84e3
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

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート