Hydrochloric Acid → HCID 58902814, compound

Participants

Reaction Steps

Titanium tetraisopropoxide (1.4 mL, 5.52 mmol) was added to a solution of 5,5-dimethyl-hexanenitrile (630 mg, 4.8 mmol) in diethyl ether (16 mL) and the resulting solution was stirred at room temperature for 10 minutes. The mixture was cooled to 0 ° C. and ethyl magnesium bromide (10 mL, 10 mmol of a 1 M solution in THF, 2.1 EQ) was added over a 20 minute period. The reaction mixture was warmed to room temperature and allowed to stir for 40 minutes after which TLC indicated complete consumption of the starting material. The solution was cooled to 0° C. and BF3.OEt2 (1.3 mL, 10.1 mmol) was added. The mixture was stirred at room temperature for 30 minutes after which aqueous HCl (2 mL of 1 N solution) and aqueous NaOH (3 mL of 3 N solution) were added. This mixture was then extracted with ethyl acetate (3×20 mL), the combined organic phases were then dried (Na2SO4), filtered, concentrated under vacuum and the residue was purified on a silica gel column (eluant methylene chloride/methanol/NH4OH, 99/1/0.1 to 90/10/1) to give 1-(4,4-dimethyl-pentyl)-cyclopropylamine. Retention time (min) =1.307, Method [1], MS (ESI) 186.2 (M+H).

Provenance & Evidence