Pyridine → HCID 90426757, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl tetrahydro-2H-pyran-4-carbimidate hydrochloride (1.646 g, 8.50 mmol) was suspended in DCM (21.25 mL) and cooled to 0° C. Pyridine (3.09 mL, 38.2 mmol) was added and the solution was stirred for 15 min. Ethyl chloroformate (1.384 g, 12.75 mmol) was added dropwise. The reaction mixture was allowed to warm to RT and stir overnight. The reaction mixture was diluted with 50% hexane/EtOAc and the resulting suspension was filtered through a plug of diatomaceous earth. The filtrate was concentrated under reduced pressure and the residue dried under high vacuum for several hours to yield ethyl N-ethoxycarbonyltetrahydro-2H-pyran-4-carbimidate (1.80 g, 92%). 1H NMR (400 MHz, DMSO-d6): δ 4.12 (m, 2H), 4.07 (m, 2H), 3.85-3.83 (m, 2H), 3.31-3.24 (m, 2H), 2.69-2.68 (m, 1H), 1.69-1.68 (m, 4H), 1.23 (m, 6H).

Provenance & Evidence