Hydrochloric Acid → HCID 86718439, compound

To a solution of 3-Methoxymethylene-9-thia-bicyclo[3.3.1]nonane (2.50 g, 13.56 mmol) in THF (35 ml) were added water (7 ml) and a 4M solution of HCl (6.78 ml, 27.10 mmol) and the reaction mixture was stirred for 16 hrs at 55° C. The reaction mixture was quenched with a saturated aqueous solution of NaHCO3, ethyl acetate was added and extracted with ethyl acetate. The organic phases were combined, washed with brine, dried using Na2SO4, filtered and concentrated in vacuo. The remaining oil was dissolved in THF/MeOH 1/1 (60 ml), DBU (0.146 g, 0.14 ml, 0.957 mmol) was added and the solution was stirred at RT for 1 hr. Ethyl acetate (150 ml), the reaction mixture was neutralized using a solution of 0.5 M HCl and extracted with ethyl acetate. The combined organic phases were washed with brine, dried using Na2SO4 and concentrated in vacuo. The crude product was purified by silica gel column chromatography (eluting with a gradient of hexanes:ethyl acetate 100:0 to 75:25) yielding the title intermediate (2.21 g, 12.33 mmol, 64%) as a colourless oil.

1. customThe reaction mixture was quenched with a saturated aqueous solution of NaHCO3, ethyl acetate
2. additionwas added
3. extractionextracted with ethyl acetate
4. washwashed with brine
5. customdried
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. dissolutionThe remaining oil was dissolved in THF/MeOH 1/1 (60 ml)
9. extractionextracted with ethyl acetate
10. washThe combined organic phases were washed with brine
11. customdried
12. concentrationconcentrated in vacuo
13. customThe crude product was purified by silica gel column chromatography (
14. washeluting with a gradient of hexanes:ethyl acetate 100:0 to 75:25)

ORD record

ord-e5ff97e633d742fa8fe6444c2ab5d216

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08859535B2