Ethanol → HCID 86761375, compound

Participants

Reaction Steps

To a stirred solution of the compound obtained from step I (0.25 g, 0.9 mmol) in a 1:1-mixture of ethanol and water (9 mL) at room temperature was added hydroxylamine hydrochloride (0.32 g, 4.5 mmol) followed by solid Na2CO3 (0.57 g, 5.4 mmol). The reaction mixture was refluxed for 12 h. The volatiles were removed under reduced pressure and the residue was dissolved in ethylacetate and washed with water. The organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure. The residue was dissolved in trimethyl orthoformate (0.2 mL) and a catalytic amount of camphor sulfonic acid was added. The reaction mixture was refluxed for 4 h. The volatiles were removed under reduced pressure and the crude product was purified by column chromatography to obtain tert-butyl [1-(1,2,4-oxadiazol-3-ylmethyl)tricyclo[3.3.1.03,7]non-3-yl]carbamate (0.15 g) in 51% yield as viscous liquid. m/z (M+1), 320; 1H NMR (CDCl3) 300 MHz δ 8.62 (s, 1H), 4.71 (bs, 1H), 2.79 (s, 2H), 2.48-2.38 (m, 1H), 2.35-2.28 (m, 1H), 2.10-1.88 (m, 4H), 1.74 (dd, J=2.8, 10.5 Hz, 2H), 1.65-1.38 (m, 4H), 1.43 (s, (H).

Provenance & Evidence