Ethanol → HCID 20748464、化合物

HRID 1760045ノート

反応式

HRID 1760045 の反応式
C(O)C.[Cl-].[NH4+].O1CCCC1.[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:22]=1[O:23][CH3:24])[CH2:19][N:18]([C:25](=[O:41])[C@@H:26]([NH:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[N+:38]([O-])=O)[C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:17][CH2:16]2>[Fe].O>[NH2:38][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[NH:31][C@@H:26]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:25]([N:18]1[CH2:17][CH2:16][C:15]2[C:20](=[CH:21][C:22]([O:23][CH3:24])=[C:13]([O:12][CH3:11])[CH:14]=2)[CH2:19]1)=[O:41]

参加物

7

反応物 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 69745485HCID 69745485、化合物

生成物 1

HCID 20748464HCID 20748464、化合物収率 87.8%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 962Water溶媒

実験手順

Ethanol (5 ml) and a saturated aqueous ammonium chloride solution (5 ml) were added to a tetrahydrofuran (5 ml) solution of (2S)-1-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)-3,3-dimethyl-2-((2-nitrophenyl)amino)butan-1-one (395 mg, 0.92 mmol) obtained in Example 24, and the mixture was stirred at room temperature. Water was added to the reaction solution until the insoluble matter was dissolved, powdery iron (6 g) was added, and the mixture was refluxed with heating for 2 hours. The reaction solution was cooled to room temperature, and the excessive iron and tinorganic salt were filtered off using Celite. The filtrate was diluted with ethyl acetate (150 ml), washed with a 1 N aqueous sodium hydroxide solution (50 ml×2), dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography using ethyl acetate and hexane (1:1) and then chloroform and methanol (20:1) as eluents to obtain the captioned compound (321 mg, 87%) as a colorless foamy substance.

後処理

  1. dissolutionwas dissolved
  2. temperaturethe mixture was refluxed
  3. temperaturewith heating for 2 hours
  4. temperatureThe reaction solution was cooled to room temperature
  5. filtrationthe excessive iron and tinorganic salt were filtered off
  6. additionThe filtrate was diluted with ethyl acetate (150 ml)
  7. washwashed with a 1 N aqueous sodium hydroxide solution (50 ml×2)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-12f112601295423eae8535460bcce31a
出典データセット
uspto-grants-2005_01
特許番号
US06838465B2

反応ノート

読み込み中…