Acetic Acid → 3-(2-ethoxycarbonylethyl)-4,5,6,7-tetrahydro-1H-indole-2-carboxylic acid ethyl ester

HRID 1860898Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1860898
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH2:6][C:7]([C:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=1[N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=O)[CH3:2].Cl.NC(C(OCC)=O)C(OCC)=[O:26].C([O-])(=O)C.[Na+].C(O)(=O)C>C(OCC)(=O)C.O>[CH2:19]([O:18][C:17]([C:16]1[NH:15][C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C:9]=2[C:7]=1[CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:21])=[O:26])[CH3:20]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 3084143Propanedioic acid, 2-amino-, 1,3-diethyl ester, hydrochloride (1:1)HCID 105899724-(2-Morpholin-4-ylcyclohex-1-enyl)-4-oxo-butyric acid ethyl ester

Produkt 1

HCID 108036583-(2-ethoxycarbonylethyl)-4,5,6,7-tetrahydro-1H-indole-2-carboxylic acid ethyl esterAusbeute 109,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Crude 4-(2-morpholin-4-ylcyclohex-1-enyl)-4-oxo-butyric acid ethyl ester (454 g), 398 g of diethyl aminomalonate hydrochloride, 162 g of sodium acetate and 350 mL of glacial acetic acid were heated to 108° C. over 30 minutes. The mixture was held at 100-108° C. for 2 hours and then cooled to about 50° C. in a water bath. Water (2500 mL) and 700 mL of ethyl acetate were added. The ethyl acetate layer was separated and washed three times with brine, twice with saturated sodium bicarbonate solutiona and once with brine. The solution was dried over anhydrous sodium sulfate, and the ethyl acetate was removed using a rotary evaporator to give 494 g (105% yield) of crude 3-(2-ethoxycarbonylethyl)-4,5,6,7-tetrahydro-1H-indole-2-carboxylic acid ethyl ester as an oil. The crude mixture was chromatographed on a silica gel column using a 1:10 mixture of ethyl acetate:hexane as the eluent to give 122.1 g of pure 3-(2-ethoxycarbonylethyl)-4,5,6,7-tetrahydro-1H-indole-2-carboxylic acid ethyl ester as a low melting solid.

Aufarbeitung

  1. customThe ethyl acetate layer was separated
  2. washwashed three times with brine
  3. dry with materialThe solution was dried over anhydrous sodium sulfate
  4. customthe ethyl acetate was removed
  5. customa rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-9ceda506f906411cb49f1d17fd4d5e52
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06531502B1

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