反应详情

Isobutylchloroformate (0.575 ml) and triethylamine (0.63 ml) were added to a solution of 4-chloro-3-[[(tricyclo[3.3.1.13,7]dec-1-ylmethyl)amino]carbonyl]-benzenepropanoic acid (Example 6c, 1.64 g) in tetrahydrofuran (30 ml) at 0° C. After 1 h the precipitates were removed by filtration and the filtrate added portionwise to a solution of sodium borohydride (0.18 g) in water (10 ml) at 0° C. After a further 1 h the reaction mixture was poured onto dilute hydrochloric acid and extracted with ethyl acetate. The organic phase was extracted twice with dilute hydrochloric acid, twice with saturated sodium hydrogencarbonate solution and once with brine, dried over magnesium sulfate and concentrated under reduced pressure to give a residue. Purification by silica gel chromatography (eluting with dichloromethane/methanol 96:4); yielded the subtitled compound as a solid (1.3 g).

1. customAfter 1 h the precipitates were removed by filtration
2. additionthe filtrate added portionwise to a solution of sodium borohydride (0.18 g) in water (10 ml) at 0° C
3. additionAfter a further 1 h the reaction mixture was poured onto dilute hydrochloric acid
4. extractionextracted with ethyl acetate
5. extractionThe organic phase was extracted twice with dilute hydrochloric acid, twice with saturated sodium hydrogencarbonate solution and once with brine
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customto give a residue
9. customPurification
10. washby silica gel chromatography (eluting with dichloromethane/methanol 96:4)