Tryptophol → 1,3,4,9-Tetrahydro-1-ethyl-pyrano[3,4-b]indole-1-acetic Acid Ethyl Ester

HRID 268662

Reaktionsgleichung

Reaktionsgleichung von HRID 268662
[CH:1]1[CH:2]=[CH:3][C:4]2[NH:9][CH:8]=[C:7]([CH2:10][CH2:11][OH:12])[C:5]=2[CH:6]=1.[C:13]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])(=O)[CH2:14][CH3:15].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:21]([O:20][C:18](=[O:19])[CH2:17][C:13]1([CH2:14][CH3:15])[C:8]2[NH:9][C:4]3[C:5]([C:7]=2[CH2:10][CH2:11][O:12]1)=[CH:6][CH:1]=[CH:2][CH:3]=3)[CH3:22]

Komponenten

5

Edukt 3

HCID 10685TryptopholHCID 78656Ethyl 3-oxovalerateHCID 521998p-Toluenesulfonic acid monohydrate

Produkt 1

HCID 691981331,3,4,9-Tetrahydro-1-ethyl-pyrano[3,4-b]indole-1-acetic Acid Ethyl EsterAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A mixture of tryptophol (1.612 g, 10 mmol), ethyl propionylacetate (1.730 g, 12 mmol), and p-toluenesulfonic acid monohydrate (0.20 g) in benzene (70 mL) was heated to reflux for 5 hours. It was quenched with ethyl acetate and washed with saturated sodium bicarbonate. The organic layer was dried over magnesium sulfate, evaporated to dryness. Flash chromatography on silica gel provided 1.943 g (68%) of the title compound as a solid. mp<80° C. 1H NMR (300 MHz, CDCl3) δ 9.06 (br, 1H), 7.50 (d, 1H), 7.36 (d, 1H), 7.14 (t, 1H), 7.12 (t, 1H), 4.18 (q, 2H), 4.03 (m, 1H), 3.94 (m, 1H), 2.99 (d, 1H), 2.88 (d, 1H), 2.78 (m, 2H), 2.14 (m, 1H), 2.01 (m, 1H), 1.25 (t, 3H), 0.82 (t, 3H); ESI (+) MS m/e=288 (MH+), ESI (−) MS m/e=286 (MH−).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 5 hours
  3. customIt was quenched with ethyl acetate
  4. washwashed with saturated sodium bicarbonate
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-d6babf1865e744da9febbf66fa31c8f4
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07446122B2

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