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Sodium Hydroxide → N-[(cis)-3-(5-fluoro-1H-indol-3-yl)cyclopentyl]-N-{[(2S)-8-methoxy-2,3-dihydro-1,4-benzodioxin-2-yl]methyl}amine

HRID 1824010
ノート
印刷プレビュー

反応式

HRID 1824010 の反応式
CC1C=CC(S(O[CH2:12][C@@H:13]2[O:18][C:17]3[C:19]([O:23][CH3:24])=[CH:20][CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)(=O)=O)=CC=1.[F:25][C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[NH:31][CH:30]=[C:29]2[C@@H:35]1[CH2:39][CH2:38][C@H:37]([NH2:40])[CH2:36]1.[OH-].[Na+]>CS(C)=O>[F:25][C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[NH:31][CH:30]=[C:29]2[C@@H:35]1[CH2:39][CH2:38][C@H:37]([NH:40][CH2:12][C@@H:13]2[O:18][C:17]3[C:19]([O:23][CH3:24])=[CH:20][CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)[CH2:36]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 14798Sodium HydroxideHCID 11792133[(2R)-8-Methoxy-2,3-dihydro-benzo[1,4]dioxin-2-yl]methyl 4-methylbenzenesulfonateHCID 68827169cis-3-(5-Fluoro-1H-indol-3-yl)-cyclopentylamine

生成物 1

HCID 10023651N-[(cis)-3-(5-fluoro-1H-indol-3-yl)cyclopentyl]-N-{[(2S)-8-methoxy-2,3-dihydro-1,4-benzodioxin-2-yl]methyl}amine収率 48%

試薬・触媒・溶媒 1

HCID 679
Dimethyl Sulfoxide
溶媒

反応条件

温度
80 °C

実験手順

A mixture of [(2R)-8-methoxy-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzene-sulfonate (0.5 g, 1.42 mmole) and cis-3-(5-fluoro-1H-indol-3-yl)-cyclopentyl-amine (0.24 g, 1.1 mmol) in anhydrous DMSO (10 mL) was heated at 80° C. for 30 h. The cooled reaction mixture was poured into 1 N aqueous NaOH (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with water (50 mL) and brine (50 mL), then were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give 0.5 g of crude product. Flash chromatography on silica gel (10% MeOH/ethyl acetate) afforded 0.2 g (48%) of the title compound as a thick oil, which was converted to its hydrochloride salt (0.195 g): MS (ESI) m/z 397 [M+H]+.

後処理

  1. customThe cooled reaction mixture
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. washThe combined organic layers were washed with water (50 mL) and brine (50 mL)
  4. dry with materialwere dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give 0.5 g of crude product

出典と根拠

ORDレコード
ord-b7de644fc0da48e5973bdb107cbfc545
出典データセット
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07041697B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート