3-Isoquinolinecarboxylic acid, 1,2,3,4-tetrahydro-, methyl ester, hydrochloride (1:1) → Decahydroisoquinoline-3-carboxylic acid, methyl ester

HRID 1702429Notes

Reaction equation

HRID 1702429 reaction equation
Cl.[CH2:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH:4]([C:12]([O:14][CH3:15])=[O:13])[NH:3]1.[H][H]>C(O)C.[Rh]>[CH2:2]1[CH:11]2[CH:6]([CH2:7][CH2:8][CH2:9][CH2:10]2)[CH2:5][CH:4]([C:12]([O:14][CH3:15])=[O:13])[NH:3]1

Participants

5

Reactant 2

HCID 122480673-Isoquinolinecarboxylic acid, 1,2,3,4-tetrahydro-, methyl ester, hydrochloride (1:1)HCID 178418361HCID 178418361, compound

Product 1

HCID 586740Decahydroisoquinoline-3-carboxylic acid, methyl esterYield 101.4%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

Procedure

Methyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride (2.3 g, 10 mmol) in 200 ml absolute ethanol is hydrogenated at 50 psi, room temperature, using 0.6 g 5% Rh/C catalyst. After the theoretical amount of hydrogen is taken up (36 hours), the catalyst is filtered and the filtrate is evaporated to dryness. The residue is dissolved in methylene chloride and washed with a saturated solution of sodium carbonate. The organic phase is dried (Na2SO4) and acidified with ethanolic HCl. Evaporation of the solvent yields 2.0 g of the product as a diastereomeric mixture which is used without further separation.

Workup

  1. customis hydrogenated at 50 psi, room temperature
  2. custom(36 hours)
  3. filtrationthe catalyst is filtered
  4. customthe filtrate is evaporated to dryness
  5. dissolutionThe residue is dissolved in methylene chloride
  6. washwashed with a saturated solution of sodium carbonate
  7. dry with materialThe organic phase is dried (Na2SO4)
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-608b49f9688e41dea7dc1f4a0e235f5c
Source dataset
uspto-grants-1983_04
Patent number
US04381302

Reaction notes

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