Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine → HCID 86679679, compound

Participants

Reaction Steps

To a solution of 3-methoxy-1H-pyrrole-2,5-dione (3 g, 24 mmol) and TFA (0.34 g, 3 mmol) in CH2Cl2 (300 mL) was added slowly a solution of N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (14.2 g, 48 mmol) in CH2Cl2 (100 mL) at a rate such to maintain the internal reaction temperature <2° C. The resulting solution was slowly warmed to ambient temperature and stirred overnight. TLC (petroleum ether/EtOAc=1/1) showed the reaction was complete. The combined five batches of reaction mixture was diluted with saturated sodium bicarbonate (100 mL), and the organics was dried over MgSO4, concentrated and purified by column chromatography (from petroleum ether/EtOAc=10/1 to petroleum ether/EtOAc=1/1) to afford title product (18 g, for 5 batches, 58% yield) as a light yellow oil, which was further purified by preparative HPLC to afford pure title product (4.5 g, 14.6% yield) as an oil.

Provenance & Evidence