(+)-Styrene oxide → (R)-4-[2-(N-benzyl-N-(2-hydroxy-2-phenylethyl)amino)ethoxy]phenylacetamide

HRID 275451

Reaktionsgleichung

Reaktionsgleichung von HRID 275451
[CH2:1]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([NH2:21])=[O:20])=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22]1[O:30][C@@H:23]1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CC(O)C>[CH2:1]([N:8]([CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][C:19]([NH2:21])=[O:20])=[CH:16][CH:17]=1)[CH2:22][C@H:23]([OH:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 114705(+)-Styrene oxideHCID 189972424-(Benzylaminoethoxy)-phenylacetamide

Produkt 1

HCID 10024191(R)-4-[2-(N-benzyl-N-(2-hydroxy-2-phenylethyl)amino)ethoxy]phenylacetamideAusbeute 64,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A mixture of 4-[2-(benzylamino)ethoxy]phenylacetamide (OLS 2135678) (14.0 g), (R)-styrene oxide (5.92 g) and propan-2-ol (200 ml) was heated under reflux for 72 hours. The mixture was cooled and the solvent evaporated under reduced pressure. The residue was purified by dry, flash column chromatography. Elution with 10% methanol in dichloromethane gave (R)-4-[2-(N-benzyl-N-(2-hydroxy-2-phenylethyl)amino)ethoxy]phenylacetamide as an oil (12.9 g). This reaction may also be performed in t-amyl alcohol under reflux.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 72 hours
  3. temperatureThe mixture was cooled
  4. customthe solvent evaporated under reduced pressure
  5. customThe residue was purified
  6. customby dry
  7. washElution with 10% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-c4df9784a09444138ccaeab1df1fb4b1
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05393779

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