反应详情

Racemic 6-methyl-spiro[2.5]octan-5-one (0.92 g, 6.656 mmol) and benzylamine (0.76 mL, 6.989 mmol) were dissolved in benzene (6 mL) and stirred at reflux with continuous removal of H2O for 3 hours. The reaction mixture was allowed to cool to RT and was diluted with DCM (30 mL). The yellow solution was cooled to 0° C. Sodium triacetoxyborohydride (95%, 1.78 g, 7.988 mmol) and acetic acid (0.5 mL, 8.65 mmol) were added. After about 20 minutes, the ice bath was removed and the suspension stirred at RT overnight. The reaction mixture was cooled to 0° C. and quenched by addition of saturated aqueous NaHCO3. The layers were separated and the aqueous layer was extracted with DCM. The combined organic layers were washed once more with saturated aqueous NaHCO3, dried (Na2SO4), filtered and evaporated. The remaining yellow oil was purified by SiO2 chromatography (100 g SiO2, DCM/(DCM:MeOH:NH4OH 60:10:1) 100 to 85% DCM) to give 0.92 g of racemic cis benzyl-(6-methyl-spiro[2.5]oct-5-yl)-amine as a light brown oil (yield 60%).

1. temperatureThe yellow solution was cooled to 0° C
2. customthe ice bath was removed
3. stirringthe suspension stirred at RT overnight
4. temperatureThe reaction mixture was cooled to 0° C.
5. customquenched by addition of saturated aqueous NaHCO3
6. customThe layers were separated
7. extractionthe aqueous layer was extracted with DCM
8. washThe combined organic layers were washed once more with saturated aqueous NaHCO3
9. dry with materialdried (Na2SO4)
10. filtrationfiltered
11. customevaporated
12. customThe remaining yellow oil was purified by SiO2 chromatography (100 g SiO2, DCM/(DCM:MeOH:NH4OH 60:10:1) 100 to 85% DCM)