反应详情

A solution of 4-[2-amino-2-(3-chloro-phenyl)-propylamino]-adamantane-1-carboxylic acid methyl ester (7.9 g) in 40 mL DCM was cooled to −20° C. and triphosgene (3.1 g) (separately dissolved in 10 mL DCM) was added to it drop wise followed by drop wise addition of triethylamine (6.57 mL). The reaction mixture was slowly brought to RT and left at stirring for 4 h. Reaction was monitored by TLC. After completion, the reaction mixture was quenched with water and the DCM layer was separated. The aqueous layer was again extracted with DCM (2×). The combined DCM layers were dried over Na2SO4 and concentrated to afford the crude product, which was purified by column chromatography to give the desired 4-[4-(3-chloro-phenyl)-4-methyl-2-oxo-imidazolidin-1-yl] adamantane-1-carboxylic acid methyl ester (5.0 g) as a mixture of E/Z isomers as a white solid. MS (ES+): 403.4 (MH+).

1. additionwas added to it drop
2. customwas slowly brought to RT
3. waitleft
4. customReaction
5. customAfter completion, the reaction mixture was quenched with water
6. customthe DCM layer was separated
7. extractionThe aqueous layer was again extracted with DCM (2×)
8. dry with materialThe combined DCM layers were dried over Na2SO4
9. concentrationconcentrated
10. customto afford the crude product, which
11. customwas purified by column chromatography