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

HRID 726662

Reaction equation

HRID 726662 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c883adf4b8604b818909113f2bd15c6c
Source dataset
uspto-grants-1998_01
Patent number
US05710130

Linked notes

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