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

HRID 1954624
ノート
印刷プレビュー

反応式

HRID 1954624 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 gas stream, lithium aluminum hydride (195.6 mg, 5.135 mmol) was suspended in dry tetrahydrofuran (40 ml). Under stirring at -15° C., a solution of ethyl cis-1-benzyl-4-(1-tert-butoxycarbonylaminocyclopropyl)-pyrrolidine-3-carboxylate (1.001 g, 2.577 mmol) in dry tetrahydrofuran (10 ml) was added dropwise thereinto over a period of 15 minutes. After stirring the reaction suspension under ice cooling for 3.5 hours, cooling water (5 ml) was slowly added thereto and the mixture was stirred at room temperature for an additional 15 minutes. The reaction suspension was filtered through celite (washed with diethyl ether). The filtrate was concentrated under reduced pressure and dried to obtain 833.9 mg (93.4%) of the title compound as a colorless oily substance.

後処理

  1. stirringAfter stirring the reaction suspension under ice cooling for 3.5 hours
  2. additionwas slowly added
  3. stirringthe mixture was stirred at room temperature for an additional 15 minutes
  4. filtrationThe reaction suspension was filtered through celite (washed with diethyl ether)
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customdried

出典と根拠

ORDレコード
ord-26ca1a53b684422e824c82f8f0d62e94
出典データセット
uspto-grants-2000_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06121285

反応ノート

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