Formaldehyde → (-)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid

HRID 2185665Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2185665
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:13]=O.S(=O)(=O)(O)O>Cl>[CH2:13]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C@@H:2]([C:10]([OH:12])=[O:11])[NH:1]1

Komponenten

5

Edukt 3

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 6140L-Phenylalanine

Produkt 1

HCID 2733226(-)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

5.0 g (30.27 mmol) of L-phenylalanine are dissolved in 50 ml of concentrated hydrochloric acid and 4.0 g of para-formaldehyde and 1 ml of concentrated sulphuric acid are added. This solution is maintained at reflux for two days. After cooling and filtration, the resulting solid is dissolved in a 1/1 (v/v) hot water/ethanol mixture and aqueous NH4OH (30%) is added until a pH 7.0 is reached. The crystals which have precipitated after cooling the solution are recovered by filtration, washed with ethanol and dried. The desired product is thus obtained.

Aufarbeitung

  1. temperatureThis solution is maintained
  2. temperatureat reflux for two days
  3. temperatureAfter cooling
  4. filtrationfiltration
  5. dissolutionthe resulting solid is dissolved in a 1/1 (v/v) hot water/ethanol mixture and aqueous NH4OH (30%)
  6. additionis added until a pH 7.0
  7. customThe crystals which have precipitated
  8. temperatureafter cooling the solution
  9. filtrationare recovered by filtration
  10. washwashed with ethanol
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-17df20052b3748889aff4fafcb5168a1
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06403561B1

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