反应详情

(2S)-2-[[N-(2-Oxo-3,3-diphenylpropyl)-(2-methoxybenzyl)amino]methyl]pyrrolidine-1-carboxylic acid benzyl ester (492 mg) was dissolved in a mixture of methanol (7.4 ml) and IN hydrochloric acid (0.5 ml), and the solution was hydrogenated over 10% palladium—charcoal (50% wet) (0.15 g) at room temperature under atmospheric pressure for 15 hours. After removal of the catalyst by filtration, the filtrate was evaporated under reduced pressure. The residue was partitioned between aqueous saturated sodium hydrogen carbonate and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixed solvent of dichloromethane and methanol (4:1). The fractions containing the objective compound were collected and evaporated under reduced pressure and the resulting residue was treated with 4N hydrogen chloride in ethyl acetate to give (8aS)-4-benzhydryloctahydropyrrolo[1,2-a]pyrazine dihydrochloride (221.2 mg) as a colorless solid.

1. customAfter removal of the catalyst
2. filtrationby filtration
3. customthe filtrate was evaporated under reduced pressure
4. customThe residue was partitioned between aqueous saturated sodium hydrogen carbonate and ethyl acetate
5. washThe organic layer was washed with brine
6. dry with materialdried over magnesium sulfate
7. customevaporated under reduced pressure
8. customThe residue was purified by column chromatography on silica gel using a mixed solvent of dichloromethane and methanol (4:1)
9. additionThe fractions containing the objective compound
10. customwere collected
11. customevaporated under reduced pressure
12. additionthe resulting residue was treated with 4N hydrogen chloride in ethyl acetate