Ammonium Hydroxide → HCID 57086846, compound

A solution of 3,14-dimethoxy-17-tetrahydrofurfurylmorphinan-6-one (9) (0.12 g, 0.31 mmol) in 10 ml of CHCl3 was added to a solution of BBr3 (0.65 g, 2.59 mmol) in 20 ml of chloroform under stirring. After 20 minutes, the product was treated with a mixture of ice (10 g), chloroform (10 ml) and NH4OH (10 ml). The resulting mixture was stirred at 0° C. for 30 minutes whereupon the layers were separated and the organic extract was washed with water. The aqueous layer was saturated with sodium chloride and re-extracted with ethyl acetate (3×15 ml). The organic extracts were combined, dried over MgSO4, filtered and concentrated under reduced pressure to provide an oily solid. The material was purified by chromatography (twice) over silica gel using graded methanol/chloroform as the eluant to give a mixture of the R and S isomers, yield 0.028 g (24.3% theory).

1. stirringThe resulting mixture was stirred at 0° C. for 30 minutes whereupon the layers
2. customwere separated
3. extractionthe organic extract
4. washwas washed with water
5. extractionre-extracted with ethyl acetate (3×15 ml)
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customto provide an oily solid
10. customThe material was purified by chromatography (twice) over silica gel using graded methanol/chloroform as the eluant
11. customto give
12. additiona mixture of the R and S isomers, yield 0.028 g (24.3% theory)

ORD record

ord-f88a9fcf3bdc41b39e9bc051a2442ef4

Source dataset

uspto-grants-1981_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04272540