Cyanogen Bromide → (2S)-2-(5-Amino-1,3,4-oxadiazol-2-yl)-1,1,1-trifluoropropan-2-ol

Participants

Reaction Steps

To a solution of (2S)-3,3,3-trifluoro-2-hydroxy-2-methylpropanohydrazide (3.0 g, 17.5 mmol) in water (17 ml) was added cyanogen bromide (1.87 g, 17.7 mmol) and potassium bicarbonate (1.82 g, 18.1 mmol). The reaction mixture was stirred 30 min at rt until a white precipitate was formed. The precipitate was filtered and washed with water followed by a mixture of ether-hexanes (1:1) to afford the title compound. 1H NMR (400 MHz, acetone-d6): δ 6.57 (bs, 2H), 6.20 (bs, 1H), 1.80 (s, 3H).

Provenance & Evidence