Benzylamine → HCID 121253854, compound

Participants

Reaction Steps

Racemic 3-methyl-tetrahydro-pyran-4-one (1 g, 8.761 mmol) was dissolved in DCM. Benzylamine (1.5 mL, 13.75 mmol) and sodium triacetoxyborohydride (95%, 3.3 g, 14.89 mmol) were added and the resulting suspension was stirred at RT overnight. The reaction mixture was washed with saturated aqueous NaHCO3. The aqueous layer was extracted with DCM. The combined organic layers were washed with brine, dried (Na2SO4), filtered and evaporated. The remaining yellow liquid was purified by SiO2 chromatography (120 g SiO2, DCM/(DCM:MeOH:NH4OH 60:10:1) 92% DCM) to give 1.8 g of racemic cis benzyl-(3-methyl-tetrahydro-pyran-4-yl)-amine as a light yellow oil (>95% yield).

Provenance & Evidence