DEDOUBLEMENT DE L'ACIDE DL-CAMPHO-10-SULFONIQUE

摘要

1391664 Resolution of dl-Camphor-10- SUlphoniC acid ELI LILLY & CO 22 June 1972 [23 June 1971] 29307/72 Heading C2C A process for the mutual resolution of dlcamphor-10-sulphonic acid and x-dl-4-dimethylamino - 1,2 - diphenyl - 3 - methyl - 2 - butanol comprises the following stages (a) reacting dlcamphor-10-sulphonic acid andα-d-4-dimethylamino-1,2-diphenyl-3-methyl-2-butanol in a 1 : 2 molar ratio in acetone, (b) separating the precipitatedα-d-4-dimethylamino-l,2-diphenyl- 3 - methyl - 2 - butanol - d - camphor - 10- sulphonate from the resolution mixture, (c) adding to the remaining resolution mixture 2 moles ofα-dl-4-dimethyl-amino-1,2-diphenyl-3- methyl-2-butanol for each mole of 1-camphor- 10- sulphonic acid present in said mixture, (d) separating the precipitated a-l-4-dimethylamino - 1,2 - diphenyl - 3 - methyl - 2 - butanoll - camphor - 10 - sulphonate from the resolution mixture, (e) separately adding to each of the salts separated in steps (b) and (d) at least an equivalent amount of a base of sufficient strength to liberate the resolving amine, (f) separating the liberated bases from the respective d- and (-camphor-10-sulphonates of the added base of step (e) and (g) separately acidifying said salts of said added base to obtain d-camphor-10-sulphonic acid and lcamphor-10-sulphonic acid respectively. The filtrates left after removal of crystalline salts in stages (b) or (d) may, in a modification of the process, be worked up directly in order to isolate and purify the l-camphor-10-sulphonic acid orα-d-4-dimethylamino-1,2-diphenyl-3- methyl-2-butanol respectively contained therein. The resolved dimethylamino- I ,2-diphenyl-3- methyl-2-butanols or their acid addition salts may be esterified to produce d or l-propoxyphene or their acid addition salts.