Imidazole → (4aR,5S,8aS)-5-(tert-Butyl-dimethyl-silanyloxy)-8a-methyl-octahydro-naphtalen-1-one

HRID 1859002

Reaktionsgleichung

Reaktionsgleichung von HRID 1859002
[OH:1][C@H:2]1[CH2:11][CH2:10][CH2:9][C@@:8]2([CH3:12])[C@H:3]1[CH2:4][CH2:5][CH2:6][C:7]2=[O:13].C([Si](Cl)(C)C)CCC.N1C=CN=C1.[Si:27](Cl)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]>CN(C)C=O>[C:30]([Si:27]([CH3:29])([CH3:28])[O:1][C@H:2]1[CH2:11][CH2:10][CH2:9][C@@:8]2([CH3:12])[C@H:3]1[CH2:4][CH2:5][CH2:6][C:7]2=[O:13])([CH3:33])([CH3:32])[CH3:31]

Komponenten

6

Edukt 4

HCID 795Imidazole2×HCID 28928tert-Butyldimethylsilyl chlorideHCID 66079N-ButylchlorodimethylsilaneHCID 21309363HCID 21309363, Verbindung

Produkt 1

HCID 21309364(4aR,5S,8aS)-5-(tert-Butyl-dimethyl-silanyloxy)-8a-methyl-octahydro-naphtalen-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 2.3 g (12.6 mMol) of (4aR,5S,8aS)-5-hydroxy-8a-methyl-octahydro-naphtalen-1-one in 63 ml of dimethylformamide are added under stirring and argon atmosphere 3.74 g (24.8 mMol) of tertio-butyl-dimethyl-silylchloride and 1.94 g (28.5 mMol) of imidazole. The reaction mixture is heated to 100° C. for 4 hours, then additional 3.74 g of tert-butyl-dimethylsilylchloride and 1.94 g of imidazole are added and the reaction mixture is kept overnight at 100° C. The reaction mixture is poured onto ice-water and extracted three times with diethylether. The combined organic extract is washed once with water and brine, dried over sodium sulfate and evaporated in vacuo. The residue is chromatographed over 250 g of silicagel with hexane/ethylacetate 9/1 to yield 3.17 g (85%) of low melting cristalline (4aR,5S,8aS)-5-(tert-butyl-dimethyl-silanyloxy)-8a-methyl-octahydro-naphtalen-1-one.

Aufarbeitung

  1. additionThe reaction mixture is poured onto ice-water
  2. extractionextracted three times with diethylether
  3. extractionThe combined organic extract
  4. washis washed once with water and brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue is chromatographed over 250 g of silicagel with hexane/ethylacetate 9/1

Quellen und Nachweise

ORD-Eintrag
ord-b4d0def3c575404bab48d32938b0fa1c
Quelldatensatz
uspto-grants-2000_11
Patentnummer
US06153605

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