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

HRID 1165977Notes

Reaction equation

HRID 1165977 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

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:

Workup

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

Sources & evidence

ORD record
ord-8c8b1083c13a4d1e80804b6e0001a43a
Source dataset
uspto-grants-1990_03
Patent number
US04912231

Reaction notes

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