Diisopropylethylamine → HCID 22115316, compound

Participants

Reaction Steps

To a solution of 3-(RS)-aminomethyl-1-tert-butoxycarbonylpyrrolidine in dichloroethane (17 mL) were sequentially added diisopropylethylamine (5.1 mL), a solution of 2-(5-bromopyrimidin-2-yloxy)acetic acid (2.9 g, 12.2 mmol, 1.1 equiv.) in tetrahydrofuran (43 mL), 1-hydroxybenzotriazole hydrate (2.4 g, 17.5 mmol, 1.5 equiv.) and 1-(3-dimethyl-aminopropyl)-3-ethylcarbodiimide hydrochloride (3.4 g, 17.6 mmol, 1.5 equiv.). The solution was stirred under N2 overnight. The reaction mixture was diluted with ethyl acetate, washed with 1 M aqueous sodium hydroxide, 1 M hydrochloric acid, water and brine, then dried over sodium sulfate and concentrated. The residue was subjected to flash chromatography to afford clean N-(1-tert-butoxycarbonylpyrrolidin-3-(RS)-ylmethyl)-2-(5-bromopyrimidin-2-yloxy)acetamide (4.2 g).

Provenance & Evidence