Sodium hydride → Benzyl 4-(2-hydroxyethyl)-3-oxopiperazine-1-carboxylate

Participants

Reaction Steps

To a solution of 1-carbobenzoxypiperazin-3-one (234 mg, 1.0 mmol) in dimethylformamide (10 ml) under nitrogen was added in one portion, 50% sodium hydride (48 mg, 1 mmol). After stirring at 20°-25° for 30 minutes until all of the sodium hydride had reacted, a solution of 2-(2-bromoethoxy)-tetrahydropyran (209 mg, 1 mmol) in dimethylformamide (2 ml) was added and the reaction mixture stirred at 20°-25° for 20 hours. Solvent was removed at 40°-45° and 0.1 mm and the residue chromatographed over silica gel. Elution with 2% isopropanol -98% methylene chloride gave the pure protected alcohol as an oil.

Provenance & Evidence