HCID 86614062, compound → 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid

HRID 1727215Notes

Reaction equation

HRID 1727215 reaction equation
C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.[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]CC2C=CC=CC=2)=[O:27])[NH:17]1>C(O)C.[Pd]>[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

Participants

4

Reactant 1

HCID 86614062HCID 86614062, compound

Product 1

HCID 954891,2,3,4-Tetrahydroisoquinoline-3-carboxylic acidYield 197.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Phenylmethyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate camphor sulphonic acid salt (Preparation 121, 8.3 g, 18.9 mmol) was dissolved in ethanol (600 ml) and palladium on carbon (10%, 0.8 g) was added at room temperature under nitrogen. The reaction mixture was hydrogenated at room temperature at 30 psi for 3 h. The catalyst was removed by filtration and the filtrate was concentrated to give the title compound (6.6 g, 100%).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-054762d0123d4ef7a54c105ab44a3c5b
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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