Pyridine → HCID 123624177, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 3-methylbutanimidate hydrochloride (4.0 g, 24.2 mmol) was suspended in DCM (48 mL) and the mixture was cooled to 0° C. Pyridine (10.0 mL, 124 mmol) was added and the mixture was stirred for 15 minutes. Ethyl chloroformate (5.3 mL, 48.3 mmol) was added and the solution was allowed to warm to RT and stirred for 12 h. The mixture was diluted with a mixture of EtOAc and hexanes (1:1, 200 mL) and solids were removed by filtration through a diatomaceous earth. The filtrate was concentrated in vacuo to afford ethyl N-ethoxycarbonyl-3-methyl-butanimidate (4.3 g, 88%) as a colorless viscous oil. 1H NMR (400 MHz, DMSO-d6): δ 4.09 (q, J=7.1 Hz, 2H), 4.05 (q, J=7.1 Hz, 2H), 2.18 (d, J=7.4 Hz, 2H), 1.95-1.94 (m, 1H), 1.20 (t, J=7.1 Hz, 3H), 1.19 (t, J=7.1 Hz, 3H), 0.86 (d, J=6.7 Hz, 6H).

Provenance & Evidence