Phenyltrimethylsilane → trans-1-Benzoyl-4-phenyl-l-proline

HRID 1165977

Reaktionsgleichung

Reaktionsgleichung von HRID 1165977
[C:1]([N:9]1[CH2:16][C@@H:15](OS(C)(=O)=O)[CH2:14][C@H:10]1[C:11]([OH:13])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]1([Si](C)(C)C)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Cl-].[Cl-].[Cl-].[Al+3]>ClC1C=CC=CC=1Cl>[C:1]([N:9]1[CH2:16][C@H:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:14][C@H:10]1[C:11]([OH:13])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 69849PhenyltrimethylsilaneHCID 6451240Aluminum(III) ChlorideHCID 11120569cis-1-benzoyl-4-((4-methylsulfonyl)oxy)-L-proline

Produkt 1

HCID 46864073trans-1-Benzoyl-4-phenyl-l-proline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 72391,2-DichlorobenzeneLösungsmittel

Versuchsvorschrift

A suspension of powdered (cis)-1-benzoyl-4-mesyloxy-L-proline (250 mg, 0.8 mmole) in 1,2-dichlorobenzene (3 ml) was stirred under argon and treated with phenyltrimethylsilane (1 ml, 5.8 mmole) followed by aluminum trichloride (383 mg, 2.87 mmole). The reaction was stirred overnight and an aliquot was removed, quenched into 1N HCl and extracted with ethyl acetate. Analysis of the organic layer by tlc showed the presence of:

Aufarbeitung

  1. stirringThe reaction was stirred overnight
  2. customan aliquot was removed
  3. customquenched into 1N HCl
  4. extractionextracted with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-8c8b1083c13a4d1e80804b6e0001a43a
Quelldatensatz
uspto-grants-1990_03
Patentnummer
US04912231

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