(2s)-Glycidyl indol-4-yl ether → (2S)-(-)-1-(4-indolyloxy)-3-[4-hydroxy-4-(naphth-1-yl)piperidine-1-yl]-2-propanol

HRID 1416204Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1416204
[O:1]1[CH2:3][C@H:2]1[CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2.[OH:15][C:16]1([C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24][CH:23]=2)[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1>CO>[NH:10]1[C:11]2[C:7](=[C:6]([O:5][CH2:4][C@@H:2]([OH:1])[CH2:3][N:19]3[CH2:18][CH2:17][C:16]([OH:15])([C:22]4[C:31]5[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=5)[CH:25]=[CH:24][CH:23]=4)[CH2:21][CH2:20]3)[CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:9]1

Komponenten

4

Edukt 2

HCID 10943254(2s)-Glycidyl indol-4-yl etherHCID 151248114-Hydroxy-4-(1-naphthyl)piperidine

Produkt 1

HCID 15409133(2S)-(-)-1-(4-indolyloxy)-3-[4-hydroxy-4-(naphth-1-yl)piperidine-1-yl]-2-propanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 0.167 gm (0.88 mMol) (S)-(+)-4-(oxiranylmethoxy)-1H-indole and 0.200 gm (0.88 mmol) 4-hydroxy-4-(naphth-1-yl)piperidine in 10 mL methanol was heated to reflux for 18 hours. The reaction mixture was cooled to room temperature and was then partitioned between ethyl acetate and 2N sodium hydroxide. The phases were separated and the aqueous phase extracted again with ethyl acetate. The organic phases were combined, washed with saturated aqueous sodium chloride and concentrated under reduced pressure. The residue was subjected to flash silica gel chromatography, eluting with 5% methanol in dichloromethane. Fractions containing product were combined and concentrated under reduced pressure to provide 0.309 (84%) of the title compound as an off-white solid.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 18 hours
  3. customwas then partitioned between ethyl acetate and 2N sodium hydroxide
  4. customThe phases were separated
  5. extractionthe aqueous phase extracted again with ethyl acetate
  6. washwashed with saturated aqueous sodium chloride
  7. concentrationconcentrated under reduced pressure
  8. washeluting with 5% methanol in dichloromethane
  9. additionFractions containing product
  10. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-50234ba1ab97432ead76c360a25beaf8
Quelldatensatz
uspto-grants-1999_06
Patentnummer
US05912256

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