Methanol → Fingolimod

Temperature

2.5 °C

2-nitro-2-(4-octylphenethyl)propane-1,3-diol (3 g) and methanol (60 mL) are charged into a hydrogenation vessel at 25-30° C. and stirred. 10% Pd/C (0.6 g) is charged into the vessel, a hydrogen pressure of 4-5 Kg/cm2 applied and the reaction mixture is maintained under the same conditions for about 5 hours. The reaction mixture is filtered through a hyflow bed and washed with methanol (10 mL). The obtained filtrate is concentrated under reduced pressure at a temperature below 36° C. to obtain 8 mL of concentrated reaction mass. n-Hexane (50 mL) is added, the reaction mixture is cooled to 0-5° C. and maintained at the same temperature for about 1 hour. The solid obtained is filtered, washed with n-hexane (10 mL) and dried under vacuum at 36° C. to give the title compound.

1. temperaturethe reaction mixture is maintained under the same conditions for about 5 hours
2. filtrationThe reaction mixture is filtered through a hyflow bed
3. washwashed with methanol (10 mL)
4. concentrationThe obtained filtrate is concentrated under reduced pressure at a temperature below 36° C.
5. customto obtain
6. custom8 mL of concentrated reaction mass
7. temperaturemaintained at the same temperature for about 1 hour
8. customThe solid obtained
9. filtrationis filtered
10. washwashed with n-hexane (10 mL)
11. customdried under vacuum at 36° C.

ORD record

ord-63ab56113bc743489c2a98e7946a16b1

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09216943B2