Isopropyl iodide → HCID 89924132, compound

Participants

Reaction Steps

A solution of 1-tert-butyl 4-methyl piperidine-1,4-dicarboxylate (0.55 g, 2.26 mmol) and 2-iodopropane (0.32 mL, 3.2 mmol) in THF (2.5 mL) was stirred at −78° C. Lithium hexamethyldisilazane (3.2 mL, 3.2 mmol) was added, then the reaction mixture was allowed to warm to ambient temperature and stirred for 18 h. The reaction mixture was partitioned between diethyl ether and brine. The ether extract was dried (MgSO4), filtered and concentrated in vacuo, to give the title compound (0.54 g, 84%) as a pale yellow syrup, which was used without further purification. δH (400 MHz, DMSO-d6) 3.86 (m, 2H), 3.68 (m, 3H), 2.69 (m, 2H), 1.99 (m, 2H), 1.68 (m, 1H), 1.53 (m, 1H), 1.36 (s, 9H), 1.28 (m, 1H), 0.80 (d, J 6.9 Hz, 6H).

Provenance & Evidence