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

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.

1. waitthe mixture kept for 24 h at 55°
2. additionThe reaction mixture was then poured
3. customonto crushed ice
4. extractionextracted twice with ether
5. washwashed with water and brine
6. dry with materialdried over sodium sulfate
7. customevaporated to dryness

ORD record

ord-67018e4ba92649e19a6b5a0809f3945d

Source dataset

uspto-grants-1999_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05919986