反应详情

To a solution of (3S,4S)-tert-butyl 3,4-dihydroxypyrrolidine-1-carboxylate (2.79 g, 13.7 mmol) in anhydrous pyridine (144 mL) was added 4,4′-(chloro(phenyl)methylene)bis(methoxybenzene) (5.43 g 15.2 mmol) and the resulting mixture stirred at ambient temperature for 4 days. The reaction was quenched with methanol (10 mL) and concentrated under reduced pressure. The residue was stirred in diethyl ether (150 mL) and the solid which precipitated was collected by filtration. The filtrate was concentrated under reduced pressure and purified by column chromatography (Biotage, 40M; 1% methanol:dichloromethane) to afford (3S,4S)-tert-butyl 3-(bis(4-methoxyphenyl)(phenyl)methoxy)-4-hydroxypyrrolidine-1-carboxylate (4.48 g, 65%).

1. customThe reaction was quenched with methanol (10 mL)
2. concentrationconcentrated under reduced pressure
3. stirringThe residue was stirred in diethyl ether (150 mL)
4. customthe solid which precipitated
5. filtrationwas collected by filtration
6. concentrationThe filtrate was concentrated under reduced pressure
7. custompurified by column chromatography (Biotage, 40M; 1% methanol:dichloromethane)