Boron trifluoride etherate → 4-(3,4-Dinitrobenzyl)morpholine

Participants

Reaction Conditions

Reaction Steps

To a mixture of (3,4-dinitro-phenyl)-morpholin-4-yl-methanone (1 mol. eq.) in dry tetrahydrofuran (THF) (25 vol.), at 0-5° C., was added NaBH4 (2 mol. eq.) followed drop-wise by BF3.Et2O (1.01 mol. eq.) so as to maintain the temperature at 0-5° C. The mixture was then stirred at ambient temperature for 3 hours and then quenched through addition of methanol. The mixture was then reduced in vacuo, partitioned between ethyl acetate and saturated aqueous NaHCO3. The mixture was stirred rapidly for 30 minutes before separating the layers. The organic layer was washed successively with water and brine before being reduced in vacuo. The product was crystallised from methanol to give 4-(3,4-dinitro-benzyl)-morpholine (85%). (LC/MS (basic method): Rt 2.80, [M+H]+ 268).

Provenance & Evidence