Formaldehyde → 3-Benzyloxy-4-dimethylaminoestra-1,3,5(10)-trien-17-one

Participants

Reaction Steps

To a suspension of 3-benzyloxy-4-aminoestra-1,3,5(10)-trien-17-one (85, 0.188 g, 0.5 mmol) in THF (1.0 mL) and CH3CN (5.0 mL) were added 37% aqueous formaldehyde (1.0 mL) and sodium cyanoborohydride (0.251 g, 4.0 mmol); the mixture was then stirred for 3 h at room temperature. Additional sodium cyanoborohydride (0.251 g, 4.0 mmol) was then added, and the mixture stirred for 24 h. Saturated aqueous NH4Cl at 0° C. was added, and the mixture extracted with EtOAc. The combined organic layers were washed with H2O, saturated aqueous NaCl, and then dried (Na2SO4). The desiccant was filtered and the solvent was evaporated at reduced pressure. The residue was purified by column chromatography (silica gel) using n-hexane:EtOAc (3:1→1:1, v/v) to afford 0.109 g of 86 (54% yield).

Provenance & Evidence