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Paper | Regular issue | Vol 43, No. 3, 1996, pp.545-550
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7285
Reduction and Carboxylation of 1-Chloromethyl-6,7-dimethoxy-3,4-dihydroisoquinolinium Salts. An Easy Entry to 1-Hydroxymethyl-1,2,3,4-tetrahydroisoquinoline Alkaloids

Rafael Suau,* Inmaculada Ruiz, Natalia Posadas, and María Valpuesta

*Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Málaga, E-29071 Málaga, Spain

Abstract

At 25 °C, the NaBH4/MeOH reduction of the title isoquinolinium salts gave the aziridine exclusively. At a low temperature (0°C) in the presence of CO2/K2CO3, the 2-oxazolidinone was obtained in almost quantitative yield. Controlled hydrolysis of the borane complex derived from the isoquinolinium salts also gave the cyclic carbamate. (±)-Calycotomine and its N-Me derivative were obtained in high yields.