Cesium carbonate → (1R,2R,4aS,8aS)-1-{[(3-methoxyphenyl)sulfanyl]methyl}-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol

HRID 422165Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 422165
CS(O[CH2:6][C@@H:7]1[C@:16]2([CH3:17])[C@H:11]([C:12]([CH3:19])([CH3:18])[CH2:13][CH2:14][CH2:15]2)[CH2:10][CH2:9][C@:8]1([OH:21])[CH3:20])(=O)=O.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([SH:30])[CH:27]=[CH:28][CH:29]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC#N>[CH3:22][O:23][C:24]1[CH:25]=[C:26]([S:30][CH2:6][C@@H:7]2[C@:16]3([CH3:17])[C@H:11]([C:12]([CH3:19])([CH3:18])[CH2:13][CH2:14][CH2:15]3)[CH2:10][CH2:9][C@@:8]2([CH3:20])[OH:21])[CH:27]=[CH:28][CH:29]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 849893-MethoxybenzenethiolHCID 58294786((1S,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl)methyl methanesulfonate

Produkt 1

HCID 58294805(1R,2R,4aS,8aS)-1-{[(3-methoxyphenyl)sulfanyl]methyl}-2,5,5,8a-tetramethyl-decahydronaphthalen-2-olAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of [(1S,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyl-decahydronaphthalen-1-yl]methyl methanesulfonate (12) (5.0 g, 16 mmol), 3-methoxybenzenethiol (1.9 mL, 16 mmol), cesium carbonate (15.3 g, 47.2 mmol) in anhydrous CH3CN (200 mL) was prepared under N2. The mixture was heated to reflux and stirred for 18 h. The reaction mixture was filtered and the filtrate concentrated to dryness. The crude product was purified by flash chromatography on silica gel (Hexanes/EtOAc, 10:1) to yield (1R,2R,4aS,8aS)-1-{[(3-methoxyphenyl)sulfanyl]methyl}-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol (13-1) (4.0 g, 71% yield) as a yellow oil.

Aufarbeitung

  1. customwas prepared under N2
  2. temperatureThe mixture was heated
  3. temperatureto reflux
  4. filtrationThe reaction mixture was filtered
  5. concentrationthe filtrate concentrated to dryness
  6. customThe crude product was purified by flash chromatography on silica gel (Hexanes/EtOAc, 10:1)

Quellen und Nachweise

ORD-Eintrag
ord-f5667bb181a641d89ca713d9bfc549c5
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101605B2

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