Imidazole → HCID 57090666, compound

Participants

Reaction Steps

A mixture of (±)-3-((αR*)-α-((2R*,5S*)-2,5-dimethyl-1-piperazinyl)benzyl)phenol (1.98 g, 6.7 mmol), from Example 38, tert-butylchlorodimethylsilane (1.51 g, 10.1 mmol), and imidazole (1.14 g, 16.8 mmol) in 30 mL of N,N-dimethylformamide was stirred at room temperature under nitrogen overnight. The reaction mixture was poured into cold water and extracted with diethyl ether. The ether extracts were dried over sodium sulfate and the solvent removed under vacuum to give a yellow oil. Chromatography on silica gel with dichloromethane:ethanol (1-7%) gave 1.68 g (61%) of (±)-(3-((αR*)-α-((2R*,5S*)-2,5-dimethyl-1-piperazinyl)benzyl)phenyl) (tert-butyldimethylsilyl) ether as a yellow oil. NMR (CDCl3, 200 MHz): δ0.1 (s, 6H); 0.9 (s, 9H); 1.05 (d, J=6 Hz, 3H); 1.2 (d, J=6 Hz, 3H); 1.7 (t, J=10 Hz, 1H); 2.45 (br m, 1H); 2.7 (m, 2H); 3.0 (m, 2H); 3.4 (br s, 1H); 5.25 (s, 1H); 6.7 (d, J=8 Hz, 1H); 6.9 (d, J=8 Hz, 1H); 7.05 (s, 1H); 7.1 (m, 3H); 7.3 (m, 3H).

Provenance & Evidence