With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.159635-49-1,tert-Butyl 4-methylenepiperidine-1-carboxylate,as a common compound, the synthetic route is as follows.
Synthesis of tert-butyl 1,1-dichloro-2-oxo-7-azaspiro[3.5]nonane-7-carboxylate; Dry DME (8.0 L) and tert-butyl 4-methylenepiperidine-1-carboxylate (800 g, 4.06 mol) were charged to a reactor. Zinc-copper couple (800 g; CAS No.53801-63-1, Alfa-Aesar) was charged to the reactor, and the mixture was warmed to 34¡ã C. Trichloroacetyl chloride (1448 g, 8.0 mol, 888 mL) was added dropwise under a nitrogen atmosphere to the stirred suspension in the following manner: 80 mL of trichloroacetyl chloride was added. After 10 min, an exotherm elevated the reaction temperature to 39¡ã C. Dropwise addition of the remaining trichloroacetyl chloride was resumed immediately at a rate to maintain a temperature between 40-44¡ã C. using a 25¡ã C. jacket. After the addition was complete, the reaction was stirred at 40¡ã C. for 15 min. Cyclohexane (10 L) was added to the mixture. The mixture was filtered through a pad of celite, washing with cyclohexane (2 L). The filtrate was concentrated to approximately 3 L and then was diluted with MTBE (3 L) and cyclohexane (2 L) and filtered through a pad of magnesol (1 kg), washing with 1:1 cyclohexane/MTBE (3 L). The filtrate was washed with saturated potassium bicarbonate (3 L) and brine (2 L). The organic layer was filtered through a pad of silica gel (300 g) with a pad of magnesol (200 g) on top. The filtrated was concentrated to yield the title compound as an orange solid (1123 g, 91percent). 1H NMR (400 MHz, CDCl3) delta ppm 4.05-4.13 (m, 2H), 3.08 (s, 2H), 2.80-2.88 (m, 2H), 1.88-1.97 (m, 2H), 1.71-1.78 (m, 2H), 1.46 (s, 9H). m/z 252, 254 (MH+ minus t-Bu)., 159635-49-1
159635-49-1 tert-Butyl 4-methylenepiperidine-1-carboxylate 2756808, apiperidines compound, is more and more widely used in various fields.
Reference£º
Patent; Pfizer Inc.; US2010/113465; (2010); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem