Ammonia → 3-(4-(((tert-Butyl(dimethyl)silyl)oxy)methyl)phenyl)-3-(trifluoromethyl)diaziridine
Reaction equation
[NH3:1].S(O[N:13]=[C:14]([C:19]1[CH:24]=[CH:23][C:22]([CH2:25][O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])=[CH:21][CH:20]=1)[C:15]([F:18])([F:17])[F:16])(C1C=CC(C)=CC=1)(=O)=O>CCOCC>[C:30]([Si:27]([CH3:28])([CH3:29])[O:26][CH2:25][C:22]1[CH:23]=[CH:24][C:19]([C:14]2([C:15]([F:16])([F:18])[F:17])[NH:13][NH:1]2)=[CH:20][CH:21]=1)([CH3:32])([CH3:33])[CH3:31]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
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).
Workup
- temperatureThe mixture was carefully cooled at −78° C.
- customThe ammonia was evaporated
- filtrationthe white precipitate was filtered
- washwashed with ether
- concentrationThe filtrate was concentrated in vacuum
Sources & evidence
- ORD record
- ord-c9fe9a8342404f2d9957bff2ad1ad6fb
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08829033B2
Reaction notes
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