Ethyl Acetate → HCID 21710516, compound

Participants

Reaction Conditions

Reaction Steps

This material is dissolved in 200 mL of methylene chloride. Proton sponge (2.5 mmol) is added in a single portion and the reaction mixture cooled to 0° C. Benzyl chloroformate (53 mmol) is added dropwise via addition funnel and the reaction mixture allowed to warm to room temperature. Stirring is continued for 2 hours at room temperature. The reaction mixture is diluted with ethyl acetate (200 mL) and washed with 1N hydrochloric acid (3×100 mL), water and brine. The organic layer is worked up to provide N-Benzyloxycarbonyl-3-acetoxymethyl-1,2,5,6-tetrahydropyridine. 1H NMR (CDCl3) δ7.40-7.25 (m, 5H), 5.90 (s, 1H), 5.14 (s, 2H), 4.47 (s, 2H), 3.95 (s, 2H), 3.54 (t, J=9.6Hz, 2H), 2.23-2.13 (m, 2H), 2.04 (s, 3H).

Provenance & Evidence