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Water → cis-1-Benzyl-4-(1-tert-butoxycarbonylaminocyclopropyl)-3-hydroxymethylpyrrolidine

HRID 635063
ノート
印刷プレビュー

反応式

HRID 635063 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 962WaterHCID 21226445Aluminium lithium hydrideHCID 69563544Ethyl cis-1-benzyl-4-(1-tert-butoxycarbonylaminocyclopropyl)pyrrolidine-3-carboxylate

生成物 1

HCID 69563790cis-1-Benzyl-4-(1-tert-butoxycarbonylaminocyclopropyl)-3-hydroxymethylpyrrolidine収率 93.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒
2 回

反応条件

温度
-15 °C

実験手順

Under a nitrogen atmosphere, lithium aluminum hydride (195.6 mg, 5.153 mmol) was suspended in anhydrous tetrahydrofuran (40 ml) to which, while stirring at −15° C., was subsequently added dropwise an anhydrous tetrahydrofuran (10 ml) solution of ethyl cis-1-benzyl-4-(1-tert-butoxycarbonylaminocyclopropyl)pyrrolidine-3-carboxylate (1.001 g, 2.577 mmol) over a period of 15 minutes. The reaction suspension was stirred for 3.5 hours in an ice bath, gradually mixed with cold water (5 ml) and then stirred for an additional 15 minutes at room temperature. The reaction suspension was filtered through celite (diethyl ether washing), and the resulting filtrate was concentrated under reduced pressure and dried, to thereby obtain 833.9 mg (93.4%) of the title compound as a colorless oil.

後処理

  1. stirringThe reaction suspension was stirred for 3.5 hours in an ice bath
  2. stirringstirred for an additional 15 minutes at room temperature
  3. filtrationThe reaction suspension was filtered through celite (diethyl ether washing)
  4. concentrationthe resulting filtrate was concentrated under reduced pressure
  5. customdried

出典と根拠

ORDレコード
ord-2b195527eea24e5c8231c6cad6f0f6f3
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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