Imidazole → (2-Aminoethoxy)(tert-butyl)dimethylsilane

Participants

Reaction Steps

1.97 mL (32.74 mmol) of 156 and 2.455 g (36.06 mmol) of imidazole were dissolved in 15 mL of CH2Cl2 and 5.18 g (34.37 mmol) of TBSCl was carefully added. After 1 h at room temperature, the mixture was concentrated and loaded on a silica gel flash chromatographic column. Elution with a mixture of 20:1 (v/v) CH2Cl2/methanol containing 0.5% (by volume) triethylamine failed to afford pure product. The eluted mixture was dissolved in water, extracted with diethyl ether (3×) and dried over sodium sulfate. Removal of the solvent yielded 1.73 g (30%) of 157 as a brown oil. 1H NMR (400 MHz, CDCl3) δ 0.06 (s, 6H), 0.90 (s, 9H), 1.74 (br s, 2H), 2.77 (t, J=5.1, 2H), 3.63 (t, J=5.2, 2H).

Provenance & Evidence