Ammonium Chloride → HCID 69958142, compound

To 110.0 mg(0.50 mmol of (3S,3aS,4R,4aS,8aR,9S, 9aR)-4,9-epoxy-3-methyl-decahydronaphtho[2,3-c]furan-1(3H)-one in 20 ml of dehydrated tetrahydrofuran solution were added dropwise 2.50 ml(5 equivalents) of lithium bis(trimethylsilyl)amide-tetrahydrofuran solution (1M) at −78° C. (internal temperature) under an atmosphere of argon, and the mixture was stirred for about 4 hours while raising temperature naturally. At −40° C., 2 ml of saturated aqueous solution of ammonium chloride were added, which was stirred at room temperature, and solvent was distilled off under reduced pressure. To the residue was added 10 ml of water, which was extracted with ether(5 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=2:1) to obtain 100.9 mg of (3S,3aS,4R,4aS,8aR)-4-hydroxy-3-methyl-3a,4,4a,5,6,7,8,8a-octahydronaphtho[2,3-c]furan-1(3H)-one (yield 92%).

1. temperaturewhile raising temperature naturally
2. stirringwhich was stirred at room temperature
3. distillationsolvent was distilled off under reduced pressure
4. additionTo the residue was added 10 ml of water, which
5. extractionwas extracted with ether(5 ml×3)
6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
7. filtrationfiltered
8. distillationsolvent was distilled off
9. customThe residue was purified by means of silica gel column chromatography(hexane:ethyl acetate=2:1)

ORD record

ord-e58833c02e954f28a85bfc710b09b897

Source dataset

uspto-grants-2002_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06392059B1