Acetic Acid → Racemic cis benzyl-(6-methyl-spiro[2.5]oct-5-yl)-amine

Participants

Reaction Steps

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%).

Provenance & Evidence