2-(Methylamino)ethanol → N-(2-(tert-Butyldimethylsilyloxy)ethyl)methylamine

Participants

Reaction Steps

2-(methylamino)ethanol (1.0 g, 13.3 mmol) was stirred in DCM (25.0 ml) under atmosphere of nitrogen. DIEA (3.23 ml, 18.6 mmol) followed by tert-butylchlorodimethylsilane (2.0 g, 13.3 mmol) was added and the reaction mixture was stirred at room temperature over night. The reaction mixture was poured into ether/water. The aqueous layer was extracted with ether three times. The combined organic layer was dried over MgSO4 and evaporated and remaining material was dried under high vacuum to afford title compound (1.4 g, yield: 56%). 1H-NMR (400 MHz, CDCl3) δ 0.08 (s, 6H) 0.91 (s, 9H) 1.93 (br. s., 1H) 2.48 (s, 3H) 2.71 (t, 2H) 3.75 (t, 2H).

Provenance & Evidence