Methanol → HCID 178421817, compound

Participants

Reaction Steps

(±)-1,1-Dimethyl-1a,3,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid ethyl ester (0.0390 g, 0.177 mmol) was stirred for 18 hours at room temperature in a solution of 1:5:1 methanol:THF:1M aqueous lithium hydroxide (14 mL). Solvent was removed under reduced pressure, the residue was taken up in 1M aqueous hydrochloric acid (5 mL) and extracted into ethyl acetate (40 mL). Solvent was removed under reduced pressure and the residue purified by preparative HPLC to give a white solid. m/z (ES+): 215 [M+Na]+, 193 [M+H]+, 175 [M−OH]+; 1H NMR (CD3CN): δ 2.91 (dd, 1H, J1=17.4, J2=6.8), 2.66 (d, 1H, J=17.4), 2.11 (dd, 1H, J1=6.3, J2=1.2), 2.05–1.95 (m, 1H), 1.19 (s, 3H, exo-CH3), 0.77 (d, 3H, J=2.0, endo-CH3).

Provenance & Evidence