HCID 69678038, Verbindung → HCID 69677833, Verbindung

HRID 1072064Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1072064
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[CH:16]=[CH:17][C@H:18]([OH:29])[C@@H:19]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCOC(C)=O.[Pd]>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[CH2:16][CH2:17][C@H:18]([OH:29])[C@@H:19]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:23])[CH3:24])[CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[OH:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[CH2:16][CH2:17][C@H:18]([OH:29])[C@@H:19]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:23])[CH3:24])[CH3:20]

Komponenten

5

Edukt 1

HCID 69678038HCID 69678038, Verbindung

Produkt 2

HCID 69677833HCID 69677833, VerbindungAusbeute 51,3 %HCID 69678558HCID 69678558, VerbindungAusbeute 45,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of (3S,4S)-1-(2-benzyloxy-4-fluorophenyl)-4-tert-butyldimethylsilyloxy-1-penten-3-ol (2.62 g) and 10% Pd—C (0.52 g) in EtOAc (65 ml) was stirred under hydrogen atmosphere at atmospheric pressure for 13 min. Pd—C was removed by filtration and the filtrate was evaporated. The residual oil (2.38 g) was chromatographed over silica gel (30 g) eluting with a mixture of hexane and EtOAc (50:1 to 2:1) to give a colorless oil of (3S,4S)-1-(2-benzyloxy-4-fluorophenyl)-4-tert-butyldimethylsilyloxy-3-pentanol (1.35 g, 51.3%) and (3S,4S)-1-(2-hydroxy-4-fluorophenyl)-4-tert-butyldimethylsilyloxy-3-pentanol (0.94 g, 45.5%).

Aufarbeitung

  1. customPd—C was removed by filtration
  2. customthe filtrate was evaporated
  3. customThe residual oil (2.38 g) was chromatographed over silica gel (30 g)
  4. washeluting with a mixture of hexane and EtOAc (50:1 to 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-70bb84863613424994efe1a9f801e6e9
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06908940B2

Notizen zur Reaktion

Wird geladen…