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

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 2-ethyl-2-hydroxybutanoate (19.7 g, 134.7 mol) and hydrazine hydrate (14 mL) was heated to 130° C. for 4 h. The mixture was cooled to rt and excess reagent removed under vacuum to yield of the hydrazide. To this hydrazide and KHCO3 (13.8 g, 138 mmol) in 150 mL of water was added portionwise BrCN (13.8 g, 131 mmol). After 90 min of stirring, the white solid was filtered, washed with ether and dried to yield the title compound. 1H NMR (400 MHz, acetone-d6): δ 6.20 (bs, 2H), 4.25 (s, 1H), 1.85 (m, 4H), 0.88 (t, 6H).

Provenance & Evidence