| 摘要 |
<p>A new process is provided herein for the preparation of the therapeutically-useful product 2,3-cis-1,2,3,4-tetrahydro-5-¢(2-hydroxy)-5-tert,butylamino)propoxyl!-2,3-naphthalenediol, a compound having Formula (I) (I) 5,8-Dihydro-1-naphthol-1-acetate is first oxidized with Nmethylmorpholine-N-oxide and a catalytic amount of osmium tetroxide to form cis-2,3-dihydroxy-1,2,3,4-tetrahydro-naphthalene-5-acetate, which is then converted with acetone to the corresponding acetonide having the Formula (V). That acetonide is reacted by a phase-transfer technique in a sodium hydroxide solution - dichloromethane mixture in the presence of a quarternary alkyl ammonium halide with epichlorohydrin to form a compound having the Formula (VI): (V) (VI), (Page 2) Reacting such compound having Formula (VI) with tert.butylamine gives the acetonide of the compound of Formula (I), which in turn is hydrolyzed to a compound having Formula (I). The compound having Formula (1), is known by the generic name NADOLOL, which has .beta.-adrenergic-blocking properties, and thus is useful in the treatment of hypertension.</p> |
