4-Toluenesulfonyl chloride → N-(4-methylbenzenesulfonyl)-octahydroisoindole-1-carboxylic acid

HRID 23884ノート

反応式

HRID 23884 の反応式
[CH:1]1([C:10]([OH:12])=[O:11])[CH:9]2[CH:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[CH2:3][NH:2]1.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH3:23][C:13]1[CH:18]=[CH:17][C:16]([S:19]([N:2]2[CH2:3][CH:4]3[CH:9]([CH2:8][CH2:7][CH2:6][CH2:5]3)[CH:1]2[C:10]([OH:12])=[O:11])(=[O:21])=[O:20])=[CH:15][CH:14]=1

参加物

5

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 13207250octahydro-1H-isoindole-1-carboxylic acid

生成物 1

HCID 22569248N-(4-methylbenzenesulfonyl)-octahydroisoindole-1-carboxylic acid収率 62.7%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

Octahydroisoindole-1-carboxylic acid (0.125 g; 0.74 mmol) from Example 1, Step A, p-toluenesulfonyl chloride (0.155 g; 0.814 mmol), and sodium carbonate (0.157 g; 1.48 mmol) were dissolved in water (3 mL). The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with water and washed with EtOAc. The water layer was acidified with concentrated. HCl and extracted with CH2Cl2 (2×50 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo to afford N-(4-methylbenzenesulfonyl)-octahydroisoindole-1-carboxylic acid (0.15 g).

後処理

  1. washwashed with EtOAc
  2. concentrationwith concentrated
  3. extractionHCl and extracted with CH2Cl2 (2×50 mL)
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-82d1effbf97645f3b2657ef9d0779921
出典データセット
uspto-grants-2005_02
特許番号
US06855708B2

反応ノート

読み込み中…