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

HRID 1912509Notes

Reaction equation

HRID 1912509 reaction equation
[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]

Participants

4

Reactant 1

HCID 31408Nopol

Product 1

HCID 228509282-((1S,2S,5S)-6,6-Dimethylbicyclo(3.1.1)heptan-2-yl)ethanolYield 91,367.797%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(−)-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.

Workup

  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

Sources & evidence

ORD record
ord-e423566131594c618d713abb4de4bd88
Source dataset
uspto-grants-2013_12
Patent number
US08609674B2

Reaction notes

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