Tetrapropylammonium → HCID 86754886, compound

Participants

Reaction Steps

459 mg of 4-methylmorpholine N-oxide, 40 mg of tetrapropylammonium perrhutenate, and 2.53 g of molecular sieves (powder, 4Å) were stirred for 0.25 h at ambient temperature. 590 mg of (1S,4aR,5R,8aR)-5-[(3E,5E )-(R)-(7-hydroxy-1,7-dimethyl-octa-3,5-dienyl)]-4a-methyl-decahydro-naphthalen-1-ol, dissolved in 5 ml of CH2Cl2, was added and the mixture kept for 2.5 h at RT. Dilution with ether, filtration over SiO2, evaporation and flash chromatography (SiO2, hexane/AcOEt=7/3) afforded 283 mg of (4aR,5R,8aR)-5-[(3E,5E)-(R)-(7-hydroxy-1,7-dimethyl-octa-3,5-dienyl)]-4a-methyl-octahydro-naphthalen]-1-one besides of 166 mg of a mixture of product and starting alcohol.

Provenance & Evidence