Vinyl Acetate → HCID 11359478, Verbindung

HRID 1870248Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1870248
[OH:1][CH2:2][CH:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:6][CH2:5][CH2:4]1.C(OC=C)(=O)C>C(OC(C)C)(C)C>[OH:1][CH2:2][C@@H:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([S:14]([C:17]2[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=2)(=[O:16])=[O:15])[CH2:6][CH2:5][CH2:4]1

Komponenten

4

Edukt 2

HCID 7904Vinyl AcetateHCID 11348115HCID 11348115, Verbindung

Produkt 1

HCID 11359478HCID 11359478, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7914Diisopropyl EtherLösungsmittel

Versuchsvorschrift

5-Hydroxymethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-benzazepine (9.94 g) is dissolved in diisopropyl ether (150 ml), and thereto are added with stirring vinyl acetate (7.75 g) and Lipase QL (8%) (0.80 g) at -2° C. The mixture is stirred at -2° C. to 1° C. for 1.5 hour. The Lipase QL is removed by filtration on celite, and the filtrate is evaporated under reduced pressure, and the resulting residue is purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=3:1→1:1) to give (5S)-5-hydroxymethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-benzazepine (hereinafter, referred to as Compound C) (4.54 g) and (5R)-5-acetyloxymethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-benzazepine (hereinafter, referred to as Compound D) (5.63 g).

Aufarbeitung

  1. customThe Lipase QL is removed by filtration on celite
  2. customthe filtrate is evaporated under reduced pressure
  3. customthe resulting residue is purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=3:1→1:1)

Quellen und Nachweise

ORD-Eintrag
ord-cb4580d3528a494384d8ce2b7086a9d8
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06096736

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