Ammonium Chloride → HCID 15427655, compound

To 9.96 g(5 equivalents) of methyltriphenylphosphonium iodide in 400 ml of dehydrated ether suspension were added dropwise 4.1 ml(5 equivalents) of sodium bis(trimethylsilyl)amide-toluene solution(0.60M) under cooling with ice and under an atmosphere of argon. After stirring for 1 hour at room temperature, 1.17 g of (1S,3S,3aR,4aS,8aR,9aS)-1-methoxy-3-methyl-4-oxo-dodecahydronaphtho[2,3-c]furan(4.93 mmol) in 30 ml of dehydrated ether solution were added dropwise again under cooling with ice. After stirring for 2 hours at room temperature, 50 ml of cold saturated aqueous solution of ammonium chloride were added to the reaction mixture and solvent was distilled off. To the residue were poured 100 ml of saturated brine, which was extracted with ether(50 ml×3). The organic layer was dried over anhydrous magnesium sulfate, filtered and solvent was distilled off. The residue was purified by means of silica gel column chromatography(hexane:ethyl acetate=10:1) to obtain 1.0 g of (1S,3S,3aS,4aS,8aR,9aS)-1-methoxy-3-methyl-4-methylene-dodecahydronaphtho[2,3-c]furan (yield 86%).

1. temperatureunder cooling with ice and under an atmosphere of argon
2. temperatureunder cooling with ice
3. stirringAfter stirring for 2 hours at room temperature
4. distillationwas distilled off
5. additionTo the residue were poured 100 ml of saturated brine, which
6. extractionwas extracted with ether(50 ml×3)
7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
8. filtrationfiltered
9. distillationsolvent was distilled off
10. customThe residue was purified by means of silica gel column chromatography(hexane:ethyl acetate=10:1)

ORD record

ord-ac7b9d13ec474ee38cb89c7884b625c8

Source dataset

uspto-grants-2002_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06392059B1