2-Nitro-2-(4-octylphenethyl)propane-1,3-diol → Fingolimod

HRID 1505027Notes

Reaction equation

HRID 1505027 reaction equation
[N+:1]([C:4]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:13][CH:12]=1)([CH2:7][OH:8])[CH2:5][OH:6])([O-])=O.[H][H]>[Pd].C(O)C>[NH2:1][C:4]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:13][CH:12]=1)([CH2:7][OH:8])[CH2:5][OH:6]

Participants

5

Reactant 2

HCID 668372762-Nitro-2-(4-octylphenethyl)propane-1,3-diolHCID 178418361HCID 178418361, compound

Product 1

HCID 107970Fingolimod

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Nitro-2-(4-octylphenethyl)propane-1,3-diol (25 g), absolute ethanol (250 mL) and 10% Pd on carbon (5 g, 50% wet) are charged into a 500 mL steel hydrogenation flask under a N2 atmosphere and the flask is equipped with a para shaker hydrogen operator. The mixture is hydrogenated with a H2 pressure of 60 psi (415 kPa) at room temperature for 2 hours and filtered through a Celite bed and washed with ethylacetate (200 mL). The filtrate is concentrated under reduced pressure at 50° C. to give the title compound as a white solid. Yield: 16 g.

Workup

  1. filtrationfiltered through a Celite bed
  2. washwashed with ethylacetate (200 mL)
  3. concentrationThe filtrate is concentrated under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-e1968369b9fd4c3989d512a4d50b817a
Source dataset
uspto-grants-2015_12
Patent number
US09216943B2

Reaction notes

Loading…