Ammonia → 3-(4-(((tert-Butyl(dimethyl)silyl)oxy)methyl)phenyl)-3-(trifluoromethyl)diaziridine

Participants

Reaction Steps

Liquid ammonia (2 mL) was added a −78° C. to an ether (15 mL) solution of 1-(4-((tert.-butyldimethylsilyloxy)methyl)phenyl)-2,2,2-trifluoroethanone O-tosyl oxime (4.00 g, 8.2 mmol) in a sealed tube. The solution was stirred at rt (16 h). The mixture was carefully cooled at −78° C. and the sealed tube was opened. The ammonia was evaporated and the white precipitate was filtered and washed with ether. The filtrate was concentrated in vacuum to obtain 2.4 g of a colorless oil (87%); NMR (CDCl3): δ 0.10 (s, (CH3)2Si), 0.95 (s, CH3)3C), 2.21 (d, J=8.1 Hz, NH), 2.77 (d, J=8.1 Hz, NH), 4.76 (s, CH2), 7.38 (d, J=8.4 Hz, 2 C6H4), 7.58 (d, J=8.4 Hz, 2 C6H4); 13C NMR (CDCl3): δ −5.3 (CH3Si), 18.4 (C(CH3)3), 25.9 (C(CH3)3), 58.0 (q, J=35.8 Hz, C diaziridine), 64.4 (CH2O), 123.6 (q, J=276.0 Hz, CF3), 126.2 (C6H2), 128.0 (C6H2), 130.2 (C6H2), 143.8 (C6H2).

Provenance & Evidence