Tetrabutylammonium Fluoride Trihydrate → (1S,4aS,8aR)-5-[(R)-5-Hydroxy-1,5-dimethyl-hex-3-ynyl]-4a-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-ol

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Reaction Steps

5.43 g (17.2 mmol) of nBu4NF.3H2O in 10 ml of THF was carefully dried by stirring during 2 h at RT over 7.5 g of 3 Å molecular sieve. This solution was then added to 866 mg (2.14 mmol) of (R)-6-[(4aR,5S,8aS)-5-(tert-butyl-dimethyl-silanyloxy)-8a-methyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-2-methyl-hept-3-yn-2-ol and the mixture kept for 24 h at 55°. The reaction mixture was then poured onto crushed ice, extracted twice with ether, washed with water and brine, dried over sodium sulfate, and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=7/3) afforded 590 mg of the title compound as colorless oil.

Provenance & Evidence