C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
C07D 491/056 (2006.01) A61K 31/4355 (2006.01) A61K 31/4741 (2006.01) A61P 31/12 (2006.01) C07D 211/40 (2006.01) C07D 491/02 (2006.01)
Patent
CA 2455018
A process is disclosed for preparation of piperidine derivatives, preferably 1,3-dioxolo [4,5-c] piperidin-7-ols such as (3aS, 4R, 7S, 7aR)-2,2,4-trimethyl- 1,3-dioxolo [4,5-c] piperidin-7-of and its polyhydroxylated derivatives. In a preferred process, 2,3-O-isopropylidene-1,4-lactone (A) is reacted with methanesulfonyl chloride to form (3aR, 4S, 6aR) methanesulfonic acid 2,2-dimethyl-6-oxo-tetrahydro- furo[3,4- d][1,3]dioxol-4-ylmethyl (B). Compound (B) is then reacted with methylmagnesium halide to form (3aR, 4S, 6aR)-methanesulfonic acid 6-hydroxy-2,2,6-trimethyl- tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester (C), which is reacted with phthalimide to form (3aR, 4S, 6aR)-2-(6-hydroxy-2,2,6-trimethyl-tetrahydro- furo[3,4- d][1,3]dioxol-4-ylmethyl)-isoindole-1,3-dione (D). Compound (D) is reacted with hydrazine to form (3S, 7S, 7aR)-2,2,4-trimethyl-3a,6,7,7a-tetrahydro- [1,3]dioxolo[4,5-c]pyridin-7-ol (E), which is hydrogenated to give the corresponding 1,3-dioxolo [4,5-c] piperidin-7-ol (F). The synthesis has an overall yield which is typically greater than 50% and avoids the use of reagents such as triflic anhydride and sodium azide.
Bydlinski Gregory
Marrugo Herika
Meunier Jean-Francois
Delmar Chemicals Inc.
Ridout & Maybee Llp
LandOfFree
Process for the preparation of piperidine derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Process for the preparation of piperidine derivatives, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the preparation of piperidine derivatives will most certainly appreciate the feedback.
Profile ID: LFCA-PAI-O-2068708