Nopol → 2-((1S,2S,5S)-6,6-Dimethylbicyclo(3.1.1)heptan-2-yl)ethanol

HRID 1912509Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1912509
[CH3:1][C:2]1([CH3:12])[CH:7]2[CH2:8][CH:3]1[CH2:4][CH:5]=[C:6]2[CH2:9][CH2:10][OH:11]>C(OCC)(=O)C.O=[Pt]=O>[CH3:1][C:2]1([CH3:12])[C@H:7]2[CH2:8][C@@H:3]1[CH2:4][CH2:5][C@H:6]2[CH2:9][CH2:10][OH:11]

Komponenten

4

Edukt 1

HCID 31408Nopol

Produkt 1

HCID 228509282-((1S,2S,5S)-6,6-Dimethylbicyclo(3.1.1)heptan-2-yl)ethanolAusbeute 91.367,797 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 345198Adams' catalystKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(−)-Nopol (Aldrich) (66.4 g 0.40 mmol) was dissolved in ethyl acetate (500 mL). PtO2 (2.0 g) was added under N2 atmosphere. The mixture was hydrogenated at 41 psi. Uptake was completed within 2.5 hours. The mixture was filtered, washed with ethyl acetate and concentrated. The residue was distilled at 125-130° C./9.5 mm of Hg. to afford 61.5 g of the title compound.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. washwashed with ethyl acetate
  3. concentrationconcentrated
  4. distillationThe residue was distilled at 125-130° C./9.5 mm of Hg

Quellen und Nachweise

ORD-Eintrag
ord-e423566131594c618d713abb4de4bd88
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609674B2

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