2-Phenylethanol → 1-(2-(6-phenethyloxy-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

HRID 13273

反応式

HRID 13273 の反応式
C(NC(C)C)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:27]1([CH2:33][CH2:34][OH:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.O[C:37]1[C:38]([CH:60]2[CH2:64][CH2:63][CH2:62][N:61]2[C:65](=[O:67])[CH3:66])=[CH:39][C:40]2[N:44]([CH2:45][O:46][CH2:47][CH2:48][Si:49]([CH3:52])([CH3:51])[CH3:50])[C:43]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][N:54]=3)=[N:42][C:41]=2[CH:59]=1.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:34]([O:35][C:37]1[C:38]([CH:60]2[CH2:64][CH2:63][CH2:62][N:61]2[C:65](=[O:67])[CH3:66])=[CH:39][C:40]2[N:44]([CH2:45][O:46][CH2:47][CH2:48][Si:49]([CH3:52])([CH3:51])[CH3:50])[C:43]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][N:54]=3)=[N:42][C:41]=2[CH:59]=1)[CH2:33][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

参加物

7

反応物 5

HCID 60542-Phenylethanol2 回HCID 7912Diisopropylamine2 回HCID 11776Triphenylphosphine2 回HCID 516892Sodium BicarbonateHCID 231452771-(2-(6-hydroxy-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

生成物 1

HCID 231455911-(2-(6-phenethyloxy-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

0.019 ml of diisopropylamine, 27.6 mg of triphenyl phosphine and 0.011 ml of 2-phenyl-ethanol were added in order to a tetrahydrofuran (1 ml) solution of 29.2 mg of 1-(2-(6-hydroxy-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)pyrrolidin-1-yl)-ethanone obtained in Example 121 (step 10), and the reaction liquid was stirred for 6 hours at room temperature. 0.040 ml of diisopropylamine, 53.2 mg of triphenyl phosphine and 0.023 ml of 2-phenyl-ethanol were added in order to the reaction liquid, and the reaction liquid was stirred overnight at room temperature. Aqueous saturated sodium bicarbonate was added to the reaction liquid, and this was extracted with ethyl acetate, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), ethyl acetate) to obtain the entitled compound as a brown oily substance.

後処理

  1. customthe reaction liquid
  2. customthe reaction liquid
  3. stirringwas stirred overnight at room temperature
  4. extractionthis was extracted with ethyl acetate
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customThe solvent was evaporated away under reduced pressure
  7. customthe resulting residue was purified
  8. customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), ethyl acetate)
  9. customto obtain the entitled compound as a brown oily substance

出典と根拠

ORDレコード
ord-50ff626390254e4b8c9004508484924c
出典データセット
uspto-grants-2010_06
特許番号
US07728025B2

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