Methanol → (2S,4R)-4-methanesulfonyloxy-1-methyl-2-(2-oxoimidazolidin-1-yl)methylpyrrolidine

To a solution of sodium borohydride (0.60 g) in tetrahydrofuran (25 ml) was added dropwise boron trifluoride ether complex (5.8 ml) under ice-cooling and the mixture was stirred at the same temperature for 15 minutes. To the mixture was added a solution of (2S,4R)-4-methanesulfonyloxy-1-methyl-2-(2-oxoimidazolidin-1-yl)carbonylpyrrolidine (2.3 g) in tetrahydrofuran (15 ml) and the mixture was stirred at the same temperature for 5 hours. To the reaction mixture was added dropwise methanol (15 ml) under ice-cooling. The mixture was filtered off and the filtrate was evaporated in vacuo. The resulting residue was dissolved in a mixture of methanol (50 ml) and conc. hydrochloric acid (2 ml) and the solution was stirred at ambient temperature overnight The reaction mixture was evaporated in vacuo to give a residue. The residue was dissolved in ethyl acetate (50 ml) and the solution was washed with saturated aqueous sodium hydrogen carbonate and aqueous sodium chloride successively, dried over anhydrous magnesium sulfate and evaporated in vacuo. The resulting residue was chromatographed on silica gel (100 g) eluting with a mixture of chloroform and methanol (9:1 V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4R)-4-methanesulfonyloxy-1-methyl-2-(2-oxoimidazolidin-1-yl)methylpyrrolidine (1.89 g).

1. temperaturecooling
2. stirringthe mixture was stirred at the same temperature for 5 hours
3. temperaturecooling
4. filtrationThe mixture was filtered off
5. customthe filtrate was evaporated in vacuo
6. dissolutionThe resulting residue was dissolved in a mixture of methanol (50 ml) and conc. hydrochloric acid (2 ml)
7. stirringthe solution was stirred at ambient temperature overnight The reaction mixture
8. customwas evaporated in vacuo
9. customto give a residue
10. washthe solution was washed with saturated aqueous sodium hydrogen carbonate and aqueous sodium chloride successively
11. dry with materialdried over anhydrous magnesium sulfate
12. customevaporated in vacuo
13. customThe resulting residue was chromatographed on silica gel (100 g)
14. washeluting with a mixture of chloroform and methanol (9:1 V/V)
15. additionThe fractions containing the desired compound
16. customwere collected
17. customevaporated in vacuo

ORD record

ord-a9590c04e5ab462aabb41eb935786953

Source dataset

uspto-grants-1990_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04925838