Isoquinoline-1-carboxylic acid → Decahydro-isoquinoline-1-carboxylic acid

HRID 1589

Reaktionsgleichung

Reaktionsgleichung von HRID 1589
[C:1]1([C:11]([OH:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[H][H]>CCO.Cl.[Rh]>[CH:1]1([C:11]([OH:13])=[O:12])[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][NH:2]1

Komponenten

6

Edukt 2

HCID 68092Isoquinoline-1-carboxylic acidHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 5232405Decahydro-isoquinoline-1-carboxylic acidAusbeute 56,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23948RhodiumKatalysatorHCID 313Hydrochloric AcidLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 1-isoquinolinecarboxylic acid (50 g, 0.288 mol) in EtOH (150 mL) and 60 mL of 5N HCl was reduced over 5% Rh/Al2O3 (14 g) at 52 bar (750 psi) of hydrogen in a high pressure apparatus at 50° C. for 17 hours. The reaction mixture was filtered through a pad of diatomaceous earth, and the filtrate was concentrated in vacuo. The solid was triturated with water, filtered and dried to give DL-perhydro-1-isoquinolinecarboxylic acid (DL-1-Piq-OH) (30 g, 48%) FD-MS 184 (MH+).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through a pad of diatomaceous earth
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe solid was triturated with water
  4. filtrationfiltered
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-e27f2076ea2944b58cddfe057fe8345b
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726159

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