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Water → Trans-1-benzyl-4-(1-tert-butoxycarbonylaminocyclopropyl)-3-hydroxymethylpyrrolidine

HRID 635059
ノート
印刷プレビュー

反応式

HRID 635059 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:18][C@@H:17]([C:19]2([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][CH2:20]2)[C@H:16]([C:30](OCC)=[O:31])[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O>O1CCCC1>[CH2:7]([N:14]1[CH2:18][C@@H:17]([C:19]2([NH:22][C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[CH2:20][CH2:21]2)[C@H:16]([CH2:30][OH:31])[CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1
参加物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 962WaterHCID 21226445Aluminium lithium hydrideHCID 69564856Ethyl trans-1-benzyl-4-(1-tert-butoxycarbonylaminocyclopropyl)pyrrolidine-3-carboxylate

生成物 1

HCID 15895249Trans-1-benzyl-4-(1-tert-butoxycarbonylaminocyclopropyl)-3-hydroxymethylpyrrolidine収率 101.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran
溶媒
2 回

実験手順

Under a nitrogen atmosphere, lithium aluminum hydride (381 mg, 9.54 mmol) was suspended in anhydrous tetrahydrofuran (30 ml) to which, while cooling in an ice bath, was subsequently added dropwise an anhydrous tetrahydrofuran (10 ml) solution of ethyl trans-1-benzyl-4-(1-tert-butoxycarbonylaminocyclopropyl)pyrrolidine-3-carboxylate (1.24 g, 3.18 mmol) over a period of 15 minutes. After 4 hours of stirring at the same temperature, ice-cooled water was gradually added to the reaction solution. The reaction suspension was subjected to celite filtration (chloroform washing) to separate the organic layer. The aqueous layer was extracted with chloroform (50 ml×2), and the organic layers were combined and dried over anhydrous sodium sulfate. By evaporating the solvent, 1.12 g (>99%) of the title compound was obtained.

後処理

  1. temperaturewhile cooling in an ice bath
  2. additionwas gradually added to the reaction solution
  3. filtrationThe reaction suspension was subjected to celite filtration (chloroform washing)
  4. customto separate the organic layer
  5. extractionThe aqueous layer was extracted with chloroform (50 ml×2)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customBy evaporating the solvent

出典と根拠

ORDレコード
ord-972f97235e694c26a4e0fa659bb0cedc
出典データセット
uspto-grants-2001_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06184388B2

反応ノート

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