Intermediate compounds and process for the preparation of fingolimod

A process for the preparation of Fingolimod of formula (I), or a pharmaceutically acceptable salt thereof, comprising the steps of:

• a) reacting octylbenzene with a 3-nitropropanoic acid derivative of formula A:
• wherein X is a halogen or an anhydride, so as to obtain 3-nitro-1-(4-octylphenyl)propan-1-one of formula (12):
• b) reducing 3-nitro-1-(4-octylphenyl)propan-1-one (12) with a reducing agent to obtain 3-nitro-1-(4-octylphenyl)propan-1-ol;
• c) protecting the hydroxyl group of 3-nitro-1-(4-octylphenyl)propan-1-ol so as to obtain compound (13A):
• wherein P is a hydroxyl protecting group;
• d) bis-hydroxymethylation of compound (13A) with formaldehyde or an equivalent thereof in the presence of catalyst, and removal of the hydroxyl protecting group to obtain compound (14):
• e) reducing compound (14) to Fingolimod (1);
• and
• f) optionally, converting Fingolimod (1) to a pharmaceutically acceptable salt thereof.