Formaldehyde → 6-Fluoro-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

HRID 340879Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 340879
[F:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[CH2:5][CH:6]([C:8]([OH:10])=[O:9])[NH2:7].[CH2:14]=O>Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:11](=[CH:12][CH:13]=1)[CH2:14][NH:7][CH:6]([C:8]([OH:10])=[O:9])[CH2:5]2

Komponenten

4

Edukt 2

HCID 712FormaldehydeHCID 99763-Fluorophenylalanine

Produkt 1

HCID 579479416-Fluoro-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a suspension of 3-fluoro-DL-phenylalanine (100 g) in conc. HCl (1.0 L) was added aq. formaldehyde solution (37% wt.; 400 mL). The reaction mixture was heated to 90° C. and stirred for 3.5 h, then cooled to RT and stirred overnight and filtered. The filtrate was concentrated and the residue was combined with the precipitate to give 6-fluoro-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, which was used without further purification. LRMS (M+H+) m/z 196.1.

Aufarbeitung

  1. temperaturecooled to RT
  2. stirringstirred overnight
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-8a11c618de6445b7ae70c11ed8937dab
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895582B2

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