Methyl morpholine oxide → 1-{(E,3S,3aS,7aR)-7-(bromomethylene)-octahydro-3a-methyl-1H-indene-3-yl}ethanone

Under a nitrogen atmosphere, a solution of (S)-1-{(E,3S,3aS,7aR)-7-(bromomethylene)-octahydro-3a-methyl-1H-indene-3-yl}ethanol (Compound 18: 58.1 mg, 0.2127 mmol) and N-methylmorpholine-N-oxide (37.4 mg, 0.3190 mmol) in acetonitrile (2 ml) was cooled in an ice bath, and tetra-n-propylammonium perruthenate (3.7 mg, 0.01064 mmol) was added thereto. The reaction mixture was stirred at the same temperature for 5 minutes, and at room temperature (22° C.) for 50 minutes, and the resulting mixture was diluted with ethyl acetate. The mixture was filtered through Celite, and the solids were washed with ethyl acetate, followed by evaporation of the filtrate under reduced pressure. The obtained crude product was purified by flash column chromatography to obtain 1-{(E,3S,3aS,7aR)-7-(bromomethylene)-octahydro-3a-methyl-1H-indene-3-yl}ethanone (58.2 mg, 100%). The spectrum data thereof agreed with the data described in Example 7.

1. waitat room temperature (22° C.) for 50 minutes
2. filtrationThe mixture was filtered through Celite
3. washthe solids were washed with ethyl acetate
4. customfollowed by evaporation of the filtrate under reduced pressure
5. customThe obtained crude product
6. customwas purified by flash column chromatography

ORD record

ord-9acd7aebe6ee4f63901222cf8c23626e

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173824B2