Formaldehyde → 1,2,3,4-Tetrahydro-6-hydroxy-3-isoquinolinecarboxylic acid

HRID 1696547Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1696547
[CH:1]1[CH:6]=[C:5]([OH:7])[CH:4]=[C:3]([CH2:8][CH:9]([NH2:13])[C:10]([OH:12])=[O:11])[CH:2]=1.[CH2:14]=O>Cl>[OH:7][C:5]1[CH:4]=[C:3]2[C:2](=[CH:1][CH:6]=1)[CH2:14][NH:13][CH:9]([C:10]([OH:12])=[O:11])[CH2:8]2

Komponenten

4

Edukt 2

HCID 712FormaldehydeHCID 130523-Tyrosine, DL-

Produkt 1

HCID 27331741,2,3,4-Tetrahydro-6-hydroxy-3-isoquinolinecarboxylic acidAusbeute 155,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a suspension of DL-m-tyrosine (5.00 g, 11.0 mmol) in 0.05 N HCl (50 mL) was added 37% aq. formaldehyde (5.00 mL, 5.2 g, 64.0 mmol) and the resulting slurry was heated at 90° C. for 1 h and then cooled to RT. The mixture was filtered and the resulting solid was washed with H2O and acetone and dried in vacuo to yield 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (3.31 g, 52% yield) as an off-white solid. MS (EI) m/z: 194.0 (M+H+). 1H NMR (400 MHz, CD3OD): δ 7.03 (d, J=8.0 Hz, 1H), 6.69 (dd, J=8.8, and 2.4 Hz, 1H), 7.00 (s, 1H), 4.28-4.19 (m, 2H), 3.80 (dd, J=11.6, and 5.2 Hz, 1H), 3.31-3.27 (m, 1H), 3.05 (dd, J=16.8, and 11.2 Hz, 1H), acid, hydroxy and amine protons not visible.

Aufarbeitung

  1. temperaturecooled to RT
  2. filtrationThe mixture was filtered
  3. washthe resulting solid was washed with H2O and acetone
  4. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3aa6456e311742c4a48a84bf1ece7df0
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163756B2

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