The
Grignard reaction between methyl 4-chlorophenylacetate [52449-43-1] (1) with
methylmagnesium iodide gives 1-(4-chlorophenyl)-2-methyl-2-propanol [5468-97-3] (2). Acylation with 2-bromopropionyl bromide [563-76-8] (3) gives [1-(4-Chlorophenyl)-2-methylpropan-2-yl] 2-bromopropanoate,
CID:13695101 (3). Displacement of halogen with ammonia leads to alaproclate (4).
^Nicholson KL, Balster RL (November 2003). "Evaluation of the phencyclidine-like discriminative stimulus effects of novel NMDA channel blockers in rats". Psychopharmacology. 170 (2): 215–24.
doi:
10.1007/s00213-003-1527-6.
PMID12851738.
S2CID30803162.
^Ulf H. A. Lindberg, Sven-Ove gren, U.S. patent 4,469,707 (1984 to Astra Lakemedel Aktiebolag).
^Lindberg, Ulf Henrik (1978). "Inhibitors of neuronal monoamine uptake. 2. Selective inhibition of 5-hydroxytryptamine uptake by .alpha.-amino acid esters of phenethyl alcohols". Journal of Medicinal Chemistry 21 (5): 448–456. doi:10.1021/jm00203a008.
^Gawell, Lars (1986). "Synthesis of [14C]alaproclate". Journal of Labelled Compounds and Radiopharmaceuticals. 23 (9): 947–949. doi:10.1002/jlcr.2580230905.
^Bengtsson, Stefan; Gawell, Lars; Högberg, Thomas; Sahlberg, Christer (1985). "Synthesis and 3H NMR of 3H-alaproclate of high specific activity". Journal of Labelled Compounds and Radiopharmaceuticals. 22 (5): 427–435. doi:10.1002/jlcr.2580220503.