Sodium ethoxide → 2-Methoxycarbonyl-(1RS,4aRS,8aRS)-perhydoisoquinoline-1-carboxylic acid ethyl ester

HRID 1594

反応式

HRID 1594 の反応式
[C:1]([O:5][C:6]([CH:8]1[CH:17]2[CH:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)[CH2:11][CH2:10][N:9]1[C:18]([O:20][CH3:21])=[O:19])=[O:7])(C)(C)[CH3:2].[O-]CC.[Na+]>CCO>[CH2:1]([O:5][C:6]([CH:8]1[CH:17]2[CH:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)[CH2:11][CH2:10][N:9]1[C:18]([O:20][CH3:21])=[O:19])=[O:7])[CH3:2]

参加物

4

反応物 2

HCID 2723922Sodium ethoxideHCID 702272422-methoxycarbonyl-(1RS,4aSR,8aSR)-perhydoisoquinoline-1-carboxylic acid t-butyl ester

生成物 1

HCID 702266492-Methoxycarbonyl-(1RS,4aRS,8aRS)-perhydoisoquinoline-1-carboxylic acid ethyl ester収率 95.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 2-methoxycarbonyl-(1RS,4aSR,8aSR)-perhydoisoquinoline-1-carboxylic acid t-butyl ester (81.2 g, 273 mmol) in EtOH (500 mL) was added sodium ethoxide (21% in ethanol) (88.4 mL, 273 mmol) and the reaction mixture was refluxed (24 h). The organic solvent was evaporated in vacuo, ethyl acetate (400 mL) and water (100 mL) was added to the residue. The organic layer was separated, washed twice with water, dried (MgSO4), filtered, and the filtrate was concentrated in vacuo to afford an oil of pure title compound (70 g,0.95%); FAB-MS 270 (MH+); TLC Rf (A) 0.61.

後処理

  1. temperaturethe reaction mixture was refluxed (24 h)
  2. customThe organic solvent was evaporated in vacuo, ethyl acetate (400 mL) and water (100 mL)
  3. additionwas added to the residue
  4. customThe organic layer was separated
  5. washwashed twice with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-270d72865aa54cd2959c3b0657ef5d22
出典データセット
uspto-grants-1998_03
特許番号
US05726159

関連ノート

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