反应详情

A mixture of 5-hexen-1-ol (5 g) and 8-azaspiro[4.5]decane-7,9-dione (14 ml) in triethylamine (150 ml) was cooled on an ice bath. Methane-sulfonyl chloride (8.6 g) in triethylamine (50 ml) was added dropwise and the mixture was stirred at room temperature for 1 hour. The mixture was filtered off and the filtrate evaporated. Dichloromethane (7.7 g), potassium carbonate (7.6 g) and N,N-dimethylformamide (100 ml) were added to the residue and the mixture was stirred at 160° C. overnight. The mixture was filtered off and the filtrate evaporated. The residue was purified by short open column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 100/0 to 98/2). The pure fractions were collected and evaporated, yielding 1.5 g (13%) of 8-(5-hexenyl)-8-azaspiro[4.5]decane-7,9-dione (interm. 8).

1. temperaturewas cooled on an ice bath
2. filtrationThe mixture was filtered off
3. customthe filtrate evaporated
4. additionDichloromethane (7.7 g), potassium carbonate (7.6 g) and N,N-dimethylformamide (100 ml) were added to the residue
5. stirringthe mixture was stirred at 160° C. overnight
6. filtrationThe mixture was filtered off
7. customthe filtrate evaporated
8. customThe residue was purified by short open column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 100/0 to 98/2)
9. customThe pure fractions were collected
10. customevaporated