HCID 10926651, compound → 149182-72-9

HRID 1657170Notes

Reaction equation

HRID 1657170 reaction equation
[C:1]([NH:5][C:6]([C@@H:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][N:9]1C(OCC1C=CC=CC=1)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([NH:5][C:6]([C@@H:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][NH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 10926651HCID 10926651, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 688344149182-72-9Yield 99.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5.7 kg of benzyl 3(S)-(t-butylcarbamoyl)-1,2,3,4-tetrahydro-2-isoquinolinecarboxylate were dissolved in 40 l of ethanol and hydrogenated in an autoclave in the presence of 1.1 kg of 10% palladium-charcoal at a pressure of 10 bar and an internal temperature of 20°-25°. After approximately 2 hours the hydrogen uptake ceased, whereupon the content of the autoclave was filtered, the autoclave and the filter residue were each rinsed twice with 20 l of ethanol each time and the combined filtrates were evaporated, whereby approximately 3.6 kg of crude N-t-butyl-1,2,3,4-tetrahydro-3(S)-isoquinoline-carboxamide were obtained as a beige solid.

Workup

  1. customan internal temperature of 20°-25°
  2. filtrationwas filtered
  3. washeach rinsed twice with 20 l of ethanol each time
  4. customthe combined filtrates were evaporated

Sources & evidence

ORD record
ord-214bff6c5f7a420eaad8e56d61bd8aaf
Source dataset
uspto-grants-1993_10
Patent number
US05256783

Reaction notes

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