4-Toluenesulfonyl chloride → Toluene-4-sulfonic acid 2-[2-(N-methyl-N-BOC-aminooxy)-ethoxy]-ethyl ester

Beteiligte Stoffe

Reaktionsschritte

To a stirred solution of 2-[2-(N-Methyl-N-BOC-aminooxy)-ethoxy]ethanol (e) 1 g (4.25 mmol) in dry DCM (15 mL) was added triethylamine (910 mg, 1254 μL, 9 mmol) and toluene-4-sulfonyl chloride (1620 mg, 8.5 mmol) in 15 mL DCM. The reaction mixture was stirred under argon overnight. TLC revealed a complete reaction (Hexane/Ethylacetate 6:4). The reaction mixture was diluted with 50 mL DCM and the organic phase was washed with NaHCO3 5%, brine and water. The organic phase was dried over MgSO4, filtered and evaporated off under reduced pressure. The product was purified using a Companion combiflash (40 g column) with a gradient of Hexane/Ethylacetate. 10-65% ethyl acetate in Hexane over 20 minutes. Structure confirmed by NMR.

Herkunft & Nachweise