Hydrochloric Acid → (2S,4R)-1-allyloxycarbonyl-4-hydroxy-2-hydroxymethylpyrrolidine

Temperature

27.5 °C

To a solution of (2S,4R)-1-allyloxycarbonyl-4-hydoxy2-methoxycarbonylpyrrolidine (10 g) in tetrahydrofuran (20 ml) and ethanol (30 ml) was added by portions sodium borohydride (3.30 g) with stirring at 25-30° C., and the mixture was stirred at the same temperature for 4 hours. To the reaction mixture was added dropwise conc. hydrochloric acid (7.27 ml) with stirring at 0-2° C. The resulting precipitates were filtered off and the filtrate was evaporated in vacuo. The resulting residue was dissolved in a mixture of tetrahydrofuran (20 ml), ethanol (20 ml) and saturated aqueous sodium chloride (50 ml). The organic layer was evaporated in vacuo to give (2S,4R)-1-allyloxycarbonyl-4-hydroxy-2-hydroxymethylpyrrolidine (9.48 g).

1. stirringthe mixture was stirred at the same temperature for 4 hours
2. stirringwith stirring at 0-2° C
3. customThe resulting precipitates
4. filtrationwere filtered off
5. customthe filtrate was evaporated in vacuo
6. dissolutionThe resulting residue was dissolved in a mixture of tetrahydrofuran (20 ml), ethanol (20 ml) and saturated aqueous sodium chloride (50 ml)
7. customThe organic layer was evaporated in vacuo

ORD record

ord-38e2bf1d102f4c5e8dc4a5901bfa2f48

Source dataset

uspto-grants-1993_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05194624