Ammonia → tert-Butyl 1-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl)ethylcarbamate

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Reaction Steps

tert-Butyl 1-(4-(2,2,2-trifluoro-1-(tosyloxyimino)ethyl)phenyl)ethylcarbamate (400 mg, 0.82 mmol) was dissolved in CH2Cl2 (5 ml). Ammonia in MeOH (7 ml, 7M) was added and the resulting mixture was stirred at room temperature for 7 days. The reaction was then diluted with water (50 ml) and extracted with CH2Cl2 (2*25 ml). Combined organics were dried over MgSO4, filtered and evaporated. The product was purified by flash chromatography using Pet. Ether/EtOAc (3:1) as eluent to give 125 mg (46%) of the title compound as white solids.

Provenance & Evidence