5-ethylimidazolidine-2,4-dione

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using 5-ethylimidazolidine-2,4-dione (1.00 g) and methyl iodide (0.51 mL) and by the reaction and treatment in the same manner as in Preparation Example 214, the title compound (0.52 g) was obtained. by the reaction and treatment in the same manner as in Preparation Example 214

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using 5-ethylimidazolidine-2,4-dione (1.00 g) and methyl iodide (0.51 mL) and by the reaction and treatment in the same manner as in Preparation Example 214, the title compound (0.52 g) was obtained. by the reaction and treatment in the same manner as in Preparation Example 214

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using 5-ethylimidazolidine-2,4-dione (2.00 g) and 4-methoxybenzyl chloride (2.54 mL) and by the reaction and treatment in the same manner as in Preparation Example 51, the title compound (3.08 g) was obtained. by the reaction and treatment in the same manner as in Preparation Example 51

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using 5-ethylimidazolidine-2,4-dione (2.00 g) and 4-methoxybenzyl chloride (2.54 mL) and by the reaction and treatment in the same manner as in Preparation Example 51, the title compound (3.08 g) was obtained. by the reaction and treatment in the same manner as in Preparation Example 51

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 5-ethylimidazoline-2,4-dione (1 g) in DMF (40 ml) was added potassium carbonate (2.16 g) followed by tert-butyl 4-[(methylsulfonyl)oxy]piperidine-1-carboxylate (2.18 g) and the resulting mixture was heated to 100° C. for 18 hours. The reaction mixture was concentrated under reduced pressure and then was partitioned between dichloromethane and water. The organic layer was collected, dried and evaporated to dryness. The residue was purified by chromatography on silica eluting with a gradient of isohexane to ethyl acetate/isohexane (1:1) to give tert-butyl 4(4-ethyl-2,5-dioxoimidazolidin-1-yl)piperidine-1-carboxylate as a solid. Yield 1.12 g. NMR (CDCl3): 0.95 (t, 3H), 1.5 (s, 9H), 1.9 (m, 2H), 2.35 (m, 2H), 2.7 (m, 2H), 3.8-4.0 (m, 3H), 4.1 (q, 2H), 5.6 (bs, 1H). The reaction mixture was concentrated under reduced pressure was partitioned between dichloromethane and water The organic layer was collected dried evaporated to dryness The residue was purified by chromatography on silica eluting with a gradient of isohexane to ethyl acetate/isohexane (1:1)