1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid camphor sulphonic acid salt → Ethyl 1,2,3,4-tetrahydro-3-isoquinolinecarboxylate

HRID 1727214Notes

Reaction equation

HRID 1727214 reaction equation
[C:1]12(CS(O)(=O)=O)C(C)(C)C(CC1)C[C:2]2=O.[CH2:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH:18]([C:26]([OH:28])=[O:27])[NH:17]1>C(O)C.Cl>[CH2:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH:18]([C:26]([O:28][CH2:1][CH3:2])=[O:27])[NH:17]1

Participants

4

Reactant 1

HCID 866140611,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid camphor sulphonic acid salt

Product 1

HCID 652898Ethyl 1,2,3,4-tetrahydro-3-isoquinolinecarboxylateYield 103.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid camphor sulphonic acid salt (Preparation 120, 6 g, 17.2 mmol) was dissolved in ethanol (140 ml) and saturated with hydrogen chloride (gas). The reaction mixture was heated under reflux for 18 h before concentrating in vacuo. The crude residue was dissolved in dichloromethane (150 ml) and washed with sodium hydrogen carbonate (150 ml). The organic layer was collected and washed again with sodium hydrogen carbonate (2×100 ml) before drying (Na2SO4) and concentrating in vacuo to give the title compound as a yellow oil (3.64 g, 100%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 18 h
  3. concentrationbefore concentrating in vacuo
  4. dissolutionThe crude residue was dissolved in dichloromethane (150 ml)
  5. washwashed with sodium hydrogen carbonate (150 ml)
  6. customThe organic layer was collected
  7. washwashed again with sodium hydrogen carbonate (2×100 ml)
  8. dry with materialbefore drying (Na2SO4)
  9. concentrationconcentrating in vacuo

Sources & evidence

ORD record
ord-b8959d5ee25743a3ac35b2d22c8dc8a6
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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