Jwh 250 → 2-(2-hydroxyphenyl)-1-(1-pentyl-1H-indol-3-yl)ethanone

HRID 61307Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 61307
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:13]=1)=[O:11]>ClCCl>[OH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:13]=1)=[O:11]

Komponenten

3

Edukt 1

HCID 44397540Jwh 250

Produkt 1

HCID 866910902-(2-hydroxyphenyl)-1-(1-pentyl-1H-indol-3-yl)ethanoneAusbeute 29,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

2-(2-Methoxyphenyl)-1-(1-pentyl-1H-indol-3-yl)ethanone (JWH-250) 4 (3 g, 8.94 mmol) was dissolved in anhydrous dichloromethane (40 ml) and cooled at −78° C. A solution of 1NBBr3 (9.83 ml, 9.83 mmol) was added dropwise and once the addition was complete the reaction mixture was allowed to warm up to room temperature and was stirred at room temperature overnight. The reaction mixture was poured into a solution of 2NHCl (100 ml) and stirred for 30 min, then extracted three times with dichloromethane (3×150 ml) and the combined organic fractions dried over sodium sulphate and concentrated in vacuo. The residue was purified by column chromatography (Biotage Isolera 4, SNAP-50 g, 0%-20% ethyl acetate in hexane) to give 840 mg (29%) of 2-(2-hydroxyphenyl)-1-(1-pentyl-1H-indol-3-yl)ethanone (O-desmethyl JWH-250) 5 as a solid.

Aufarbeitung

  1. additionA solution of 1NBBr3 (9.83 ml, 9.83 mmol) was added dropwise
  2. additiononce the addition
  3. temperatureto warm up to room temperature
  4. additionThe reaction mixture was poured into a solution of 2NHCl (100 ml)
  5. stirringstirred for 30 min
  6. extractionextracted three times with dichloromethane (3×150 ml)
  7. dry with materialthe combined organic fractions dried over sodium sulphate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography (Biotage Isolera 4, SNAP-50 g, 0%-20% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-344a8cb10cd14784be1c49bc42103ae5
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09441033B2

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