3-METHYL-3-AZETIDINECARBONITRILE HYDROCHLORIDE synthesis

Yield:936850-33-8 92%

Reaction Conditions:

Stage #1: tert-butyl 3-cyano-3-methylazetidine-1-carboxylatewith 2,2,2-trifluoroethanol at 150; for 4 h;Microwave irradiation;Inert atmosphere;
Stage #2: with hydrogenchloride in diethyl ether at 0;

Steps:

95.2

Step 2 A 20 mL microwave vial was charged with 3-cyano-3-methyl-azetidine-1-carboxylic acid tert-butyl ester (0.75 g, 3.82 mmol) and 2,2,2-trifluoroethanol (15.0 mL, 206 mmol). The vial was flushed with Argon and closed. The colorless solution was heated at 150° C. for 4 h under microwave irradiation. The reaction mixture was cooled to 0° C. and hydrogen chloride (1.0M solution in diethyl ether, 4.6 mL, 4.6 mmol) was added dropwise. The light yellow solution was concentrated and the residue was triturated with diethyl ether to afford 466 mg (92%) of 3-cyano-3-methyl-azetidine hydrochloride as a light yellow powder.

References:

US2011/230462,2011,A1 Location in patent:Page/Page column 90