4-Methylmorpholine → HCID 15427654, compound

Also, the synthesis was possible separately through following process. Namely, 0.77 g(1.50 equivalents) of N-methylmorpholine and 2.50 g of molecular sieve 4A(MS4A) were added to 1.05 g(4.37 mmol) of (1S,3S,3aS,4R,4aS,8aR,9aS)-4-hydroxy-1-methoxy-3-methyl-dodecahydronaphtho[2,3-c]furan in 10 ml of methylene chloride solution, then 76.8 mg(0.05 equivalents) of tetrapropylammonium perruthenate(TPAP) were added, and the mixture was stirred for 1.5 hours at room temperature. The reaction mixture was filtered through celite and the residue was washed with ether(100 ml). The filtrate was washed with 10% aqueous solution of Na2S2O3 and then with brine (each 20 ml×1). The organic layer was dried over anhydrous magnesium sulfate, filtered and solvent was distilled off to obtain 0.99 g of (1S,3S,3aR,4aS,8aR,9aS)-1-methoxy-3-methyl-4-oxo-dodecahydronaphtho[2,3-c]furan (yield 95%).

1. filtrationThe reaction mixture was filtered through celite
2. washthe residue was washed with ether(100 ml)
3. washThe filtrate was washed with 10% aqueous solution of Na2S2O3
4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
5. filtrationfiltered
6. distillationsolvent was distilled off

ORD record

ord-e7fa71d396374f96825b297f513d1fc1

Source dataset

uspto-grants-2002_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06392059B1