Water → (1S,4aR,5R,8aR)-5-[(R)-5-Hydroxy-1,5-dimethyl-hexyl]-4a-methyl-decahydro-naphtalen-1-ol

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Reaction Steps

To a stirred solution of 267 mg (0.65 mMol) of (R)-6-[(1R,4aR,5S,8aR)-5-(tert-butyl-dimethyl-silanyloxy)-8a-methyl-decahydronaphtalen-1-yl]-2-methyl-heptan-2-ol in 2.5 ml of tetrahydrofuran are added 7.5 ml of acetonitrile and 2.5 ml of an aqueous HF solution (40%). The reaction mixture is kept for 72 hours, poured unto water and extracted three times with diethylether, the combined organic extracts are washed with a saturated aqueous NaHCO3 solution, with water, dried over Na2SO4, filtered and evaporated in vacuo. The residue is chromatographed over 40 g of silicagel with toluene/diethylether 4/1 to yield 107 mg (56%) of crystalline pure (1S,4aR,5R,8aR)-5-[(R)-5-Hydroxy-1,5-dimethyl-hexyl]-4a-methyl -decahydro-naphtalen-1-ol. The material crystallized with diisopropylether has m.p.: 85.1-86.9°.

Provenance & Evidence