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

HRID 13273

Reaction equation

HRID 13273 reaction equation
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

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-50ff626390254e4b8c9004508484924c
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Linked notes

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