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

Temperature

40 °C

To a suspension of sodium borohydride (5 g) in ethanol (50 ml) was added (2S,4R)-1-allyloxycarbonyl-2-methoxycarbonyl-4-hydroxypyrrolidine (10 g) in ethanol (10 ml) at 5° C. and the resulting mixture was stirred at 40° C. for 4 hours. After cooling to 0° C., the reaction mixture was added dropwise to cooled acetone (20 ml) at 10° C. The mixture was evaporated in vacuo and the residue was extracted with ethyl acetate (200 ml×2). The organic layer was washed with brine, dried over magnesium sulfate, evaporated and chromatographed on silica gel (120 ml) eluting with a mixture of n-hexane and ethyl acetate (1:1 V/V) to give (2S,4R)-1-allyloxycarbonyl-4-hydroxy-2-hydroxymethylpyrrolidine (4.45 g).

1. temperatureAfter cooling to 0° C.
2. additionthe reaction mixture was added dropwise
3. customThe mixture was evaporated in vacuo
4. extractionthe residue was extracted with ethyl acetate (200 ml×2)
5. washThe organic layer was washed with brine
6. dry with materialdried over magnesium sulfate
7. customevaporated
8. customchromatographed on silica gel (120 ml)
9. washeluting with a mixture of n-hexane and ethyl acetate (1:1 V/V)

ORD record

ord-e24469f66ae2416fa7528294fc763706

Source dataset

uspto-grants-1990_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04923857