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Indole-3-Acetic Acid → (1H-Indol-3-yl)-acetic acid 4-dimethylamino-4-phenyl-cyclohexyl ester hydrochloride

HRID 1349398
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1349398
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([OH:13])=[O:12])=[CH:2]1.[CH3:14][N:15]([CH3:29])[C:16]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:21][CH2:20][CH:19](O)[CH2:18][CH2:17]1.C1(N=C=NC2CCCCC2)CCCCC1.[Cl:45][Si](C)(C)C>CN(C)C1C=CN=CC=1.CC(=O)CC.O.C1COCC1.ClCCl>[ClH:45].[CH3:14][N:15]([CH3:29])[C:16]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:17][CH2:18][CH:19]([O:12][C:11](=[O:13])[CH2:10][C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)[CH2:20][CH2:21]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 4

HCID 802Indole-3-Acetic AcidHCID 6397ChlorotrimethylsilaneHCID 10868DicyclohexylcarbodiimideHCID 111487094-Dimethylamino-4-phenylcyclohexanol

Produkt 1

HCID 69423004(1H-Indol-3-yl)-acetic acid 4-dimethylamino-4-phenyl-cyclohexyl ester hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 14284
4-(Dimethylamino)pyridine
Katalysator
HCID 962WaterLösungsmittel
HCID 6344DichloromethaneLösungsmittel
HCID 6569Methyl Ethyl KetoneLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

175 mg of (1H-indol-3-yl)-acetic acid and 219 mg of 4-dimethylamino-4-phenyl-cyclohexanol (mixture of diastereoisomers analogously to Example 4) were added, under argon and while cooling with ice, to a mixture of 5 ml of dry dichloromethane and 5 ml of dry THF with 206 mg of dicyclohexylcarbodiimide and 12 mg of 4-dimethylaminopyridine, and stirring was carried out overnight. The resulting solid was filtered and washed with a small amount of diethyl ether. The resulting filtrate was concentrated and the residue was stirred for five minutes with a mixture of 10 ml of each of two molar sodium hydrogen carbonate solution and ethyl acetate. The phases were separated, the aqueous phase was extracted three times using 10 ml of ethyl acetate each time, and the combined organic phases were washed with 10 ml of water, dried over sodium sulfate and concentrated. The residue obtained was a mixture of the two possible diastereoisomeric esters, which were separated by chromatography on silica gel with methanol. 60 mg of the non-polar and 108 mg of the polar diastereoisomer were obtained in the form of colourless oils which, as described for Example 1, were converted into 65 mg (Example 13) and 118 mg (Example 14) of the corresponding hydrochlorides using chlorotrimethylsilane and water in 2-butanone.

Aufarbeitung

  1. additionwere added, under argon
  2. filtrationThe resulting solid was filtered
  3. washwashed with a small amount of diethyl ether
  4. concentrationThe resulting filtrate was concentrated
  5. stirringthe residue was stirred for five minutes with a mixture of 10 ml of each of two molar sodium hydrogen carbonate solution and ethyl acetate
  6. customThe phases were separated
  7. extractionthe aqueous phase was extracted three times
  8. washthe combined organic phases were washed with 10 ml of water
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated
  11. customThe residue obtained
  12. customwere separated by chromatography on silica gel with methanol
  13. custom60 mg of the non-polar and 108 mg of the polar diastereoisomer were obtained in the form of colourless oils which

Quellen und Nachweise

ORD-Eintrag
ord-3261d23dc5284ec58340677a72786507
Quelldatensatz
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07211694B2

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