PROCEDIMIENTO PARA LA OBTENCION DE 3,4-DIHIDROXIFENILALKA- NOLAMINAS.

摘要

1,204,195. Phenylalkanolamine derivatives. BOEHRINGER INGELHEIM G.m.b.H. 18 Oct., 1967 [18 Oct., 1966; 20 Oct., 1966; 29 Nov., 1966], No. 47491/67. Heading C2C. Racemic and optically active compounds of the general formula (R 1 = H, acyl; R 2 =C 1-5 alkyl or alkoxy, C 5-6 cycloalkyl; R 3 = H, C 1-4 alkyl; K 4 = C 1-8 alkyl, cyoloalkyl containing up to 7 carbon atoms, benzodioxan-2-yl-(C 1-3 alkyl) or wherein Z = C 2-6 alkylene; n = 0, 1; R 5,6 = H, OH, C 1-4 alkyl or alkoxy or R 5 + 6 = OCH 2 O; provided that R 4 is not Pri if R 1 = H, R 2 = Me, MeO and R 3 = H, Me, Et) and their salts are prepared by (a) reducing a compound of the formula (R1 = R 1 or protecting group or OR1R1O = acetal group; R11 = H or protecting group); (b) reducing a compound of the formula (R 7 = CO, CHOH) in the presence of R 4 NH 2 or, when R, = CHOH, condensing the two reactants and reducing the product; (c) reacting a compound of the formula (E = oxiranyl or alkyloxiranyl and/or 2; halo-1- hydroxyalkyl) with R 4 R11NH; (d) reacting a compound of the formula under reducing conditions with R 8 R 9 CO (R 8 = H or straight chain C 1-4 alkyl, R 9 = alkyl, sum of carbon atoms in R 8 + 9 is not more than 7, or R 9 = 1,4-benzodioxan-2-yl, 1,4-benzodioxan- 2 - ylmethyl, 1,4 - benzodioxan - 2 - ylethyl or wherein Z1 = alkylene, sum of carbon atoms in Z1 and R 8 is not more than 5, or R 8 + 9 = alkylene containing up to 6 carbon atoms); (e) -when R 3 = H-reducing a compound of the formula or (f) reacting a compound of the formula with a reactive ester of R 4 OH, optionally followed in each case by salt formation and/or resolution. The preparation of starting materials for processes (a)-(f) by standard methods and of 2 - ethoxy - 3,4 - diphenylmethylenedioxyacetophenone, 3 - allyloxy - 4 - methoxyacetophenone, 2 - allyl - 3 - hydroxy - 4 - methoxyacetophenone- 2 - propyl - 3 - hydroxy - 4 - methoxyacetophenone, 2 - propyl - 3 - acetoxy - 4 - methoxybromoacetophenone,α- bromo - 2 - methyl - 3,4 - dimethoxyacetophenone, 2 - hydroxy - 3,4 - diphenylmethylenedioxyacetophenone, 2 - methoxy - 3,4 - diphenylmethylenedioxyacetophenone,α- bromo- 2 - methoxy - 3,4 - diphenylmethylenedioxyacetophenone, 2 - methoxy - 3,4 - diphenylmethylenedioxybutyrophenone andα- bromo - 2 - methoxy- 3,4 - diphenylmethylenedioxybutyrophenone is described. The compounds of the invention are sympathomimetics, and may be administered in the form of pharmaceutical preparations containing them in association with a carrier.