Water → HCID 73191471, compound

Participants

Reaction Conditions

Reaction Steps

In a flame dried flask equipped with a magnetic stirring rod and a rubber septum with a N2 inlet was added (S,S) 3-hydroxymethylaziridine-2-carboxylic acid ethyl ester (296 mg, 2.04 mmol) and 12 ml of CH2Cl2. The reaction vessel was cooled to 0° C. then TBDMSCl (377 mg, 2.50 mmol) and DMAP (623 mg, 5.1 mmol) was added. The reaction was allowed to stir for 1 hour at 0° C. then at room temperature until the reaction was completed according to TLC (Rf=0.65; 7:3 hexanes/EtOAc). The reaction was diluted with CH2Cl2 then water was added. The organic layer was extracted three times, and the combined organic layers were washed first with saturated NaHCO3, then water, then brine and dried over solid Na2SO4. The mixture was filtered and dried under reduced pressure to afford a pale yellow oil, which was subjected to flash column chromatography (silica gel; 8:2 hexanes/EtOAc) to afford the title compound as a thick colourless oil in 99% yield. 1H NMR (CDCl3, 400 MHz) δ: 4.21 (q, J=3.6 Hz, 2H), 3.66 (dd, J=11.2 Hz, 5.2 Hz, 1H), 3.56 (dd, 10.8 Hz, 4.8 Hz, 1H), 2.42 (m, 2H), 1.37 (bt, 1H), 1.29 (t, J=7.2 Hz, 3H) ppm. 13C NMR (CDCl3, 100 MHz) δ: 172.6, 64.8, 61.7, 40.3, 33.7, 26.1, 18.5, 14.4, −5.1 ppm. HRMS (ESI) [M+H]+ calcd. for C12H25NO3Si 260.1676, found 260.1675.

Provenance & Evidence