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

HRID 1165977ノート

反応式

HRID 1165977 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 72391,2-Dichlorobenzene溶媒

実験手順

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:

後処理

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

出典と根拠

ORDレコード
ord-8c8b1083c13a4d1e80804b6e0001a43a
出典データセット
uspto-grants-1990_03
特許番号
US04912231

反応ノート

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