Dimethyl Sulfide → HCID 53323813, compound

Temperature

70 °C

To the refluxing solution of N-{1-[1-(3,4-dichloro-phenyl)-cyclohexyl]-ethyl}-formamide (5.2 g, 17.32 mmol) in anhydrous THF (75 mL) was added slowly BH3.SMe2 (2N solution in THF, 26 mL, 51.96 mmol). The solution was stirred at 70° C. for 20 mins then a distillation head was installed. The solution was refluxed for 2 h, during which SMe2 was distilled, and the solution was cooled to R.T. and concentrated using a rotary evaporator. The pale yellow residue was cooled to 0° C. and added slowly to methanol (20 mL) to destroy the excess borane. The resulting clear solution was added to 6N aqueous HCl (50 mL) and heated to reflux for 40 minutes, then cooled to room temperature. The solid that formed was filtered and washed with water (2×50 mL), followed by slurrying in ethyl ether (200 mL) and filtration to give 48 E1 as a white solid. (4.04g, 72.5%). Note: Same reaction was run on a 50 g scale with 70% yield.

1. distillationwas distilled
2. temperaturethe solution was cooled to R.T.
3. concentrationconcentrated
4. customa rotary evaporator
5. temperatureThe pale yellow residue was cooled to 0° C.
6. additionadded slowly to methanol (20 mL)
7. customto destroy the excess borane
8. additionThe resulting clear solution was added to 6N aqueous HCl (50 mL)
9. temperatureheated
10. temperatureto reflux for 40 minutes
11. temperaturecooled to room temperature
12. customThe solid that formed
13. filtrationwas filtered
14. washwashed with water (2×50 mL)
15. filtrationfiltration

ORD record

ord-44fb67b4fc784bd0a8000e5e77dbd066

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08877975B2