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2-(4-Phenylbutyl)phenol → (4R)-4-Benzyloxy-1-t-butoxycarbonyl-2-[2-(4-phenylbutyl) phenoxymethyl]pyrrolidine

HRID 743242
ノート
印刷プレビュー

反応式

HRID 743242 の反応式
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[OH:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].[CH2:24]([O:31][C@H:32]1[CH2:36][N:35]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH:34]([CH2:44]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:33]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CC(N(C)C)=O>[CH2:24]([O:31][C@H:32]1[CH2:36][N:35]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH:34]([CH2:44][O:17][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][CH2:9][CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:33]1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 125964892-(4-Phenylbutyl)phenolHCID 23665647Potassium tert-butoxideHCID 53856550(4R)-4-benzyloxy-1-t-butoxycarbonyl-2-(p-toluenesulfonyloxymethyl)pyrrolidine

生成物 1

HCID 54385681(4R)-4-Benzyloxy-1-t-butoxycarbonyl-2-[2-(4-phenylbutyl) phenoxymethyl]pyrrolidine収率 24.1%

試薬・触媒・溶媒 1

HCID 31374
Dimethylacetamide
溶媒

反応条件

温度
40 °C

実験手順

441 mg of 2-(4-phenylbutyl)phenol (prepared as described in Preparation 3) and 241 mg of potassium t-butoxide were dissolved, with ice-cooling and stirring, in 20 ml of dimethylacetamide. 900 mg of (4R)-4-benzyloxy-1-t-butoxycarbonyl-2-(p-toluenesulfonyloxymethyl)pyrrolidine were then added to the solution thus obtained, and the resulting mixture was stirred at 40° C. for 5 hours. At the end of this time, the reaction mixture was cooled and partitioned between ethyl acetate and water. The organic layer was dried over anhydrous sodium sulfate, and concentrated by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel, using a 4:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 242 mg (yield 24%) of the title compound as a colorless oil.

後処理

  1. temperaturecooling
  2. customthus obtained
  3. temperatureAt the end of this time, the reaction mixture was cooled
  4. custompartitioned between ethyl acetate and water
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customThe residue was purified by column chromatography through silica gel
  8. additionby volume mixture of hexane and ethyl acetate as the eluent

出典と根拠

ORDレコード
ord-ff2566da914b45f0b68d997e5fe8bd93
出典データセット
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05556864

反応ノート

読み込み中…

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