Tryptophol → 1-Methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-propionic acid

HRID 1833694

Reaktionsgleichung

Reaktionsgleichung von HRID 1833694
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11]S)=[CH:2]1.C1C=CC2NC=C(CCO)C=2C=1.[C:25]([OH:32])(=[O:31])[CH2:26][CH2:27][C:28]([CH3:30])=[O:29].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C1C=CC=CC=1>[CH3:30][C:28]1([CH2:27][CH2:26][C:25]([OH:32])=[O:31])[C:2]2[NH:1][C:9]3[C:4]([C:3]=2[CH2:10][CH2:11][O:29]1)=[CH:5][CH:6]=[CH:7][CH:8]=3

Komponenten

6

Edukt 4

HCID 10685TryptopholHCID 11579Levulinic AcidHCID 14812Phosphorus oxide (P4O10)HCID 122442792-(1H-indol-3-yl)ethane-1-thiol

Produkt 1

HCID 122045301-Methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-propionic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A mixture of the starting material of formula II, tryptophol (500 mg.), levulinic acid (580 mg.), 75 ml. of benzene, 1.7 g. of phosphorus pentoxide and about 0.5 g. of diatomaceous earth (Celite) is stirred magnetically at room temperature for 15 minutes and then at 70° C. for 11/2 hr. The reaction mixture is filtered. The filtrate is washed three times with 5N NaOH; the combined aqueous phase is washed twice with ether and then rendered acidic with cold 50% HCl. The aqueous phase is extracted with chloroform. The chloroform extract is dried (Na2SO4) and evaporated to dryness. The residue is crystallized from ethyl acetate-petroleum ether to afford the title compound, m.p. 104° - 110° C., nmr (CDCl3) δ1.47 (3H), 2.18 (4H), 2.74 (2H), 3.96 (2H), 7.18 (1H), 9.60 (1H).

Aufarbeitung

  1. customat 70° C.
  2. custom2 hr
  3. filtrationThe reaction mixture is filtered
  4. washThe filtrate is washed three times with 5N NaOH
  5. washthe combined aqueous phase is washed twice with ether
  6. extractionThe aqueous phase is extracted with chloroform
  7. extractionThe chloroform extract
  8. dry with materialis dried (Na2SO4)
  9. customevaporated to dryness
  10. customThe residue is crystallized from ethyl acetate-petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-f82c7b4c2ac949778642fd8aef072a1d
Quelldatensatz
uspto-grants-1978_01
Patentnummer
US04066780

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