Water → HCID 57026776, compound

To a solution of (2S,4R)-1-allyloxycarbonyl-4-t-butyldimethylsilyloxy-2-(2-methyl-3-oxo-1-butenyl)-pyrrolidine (9.9 g) in tetrahydrofuran (99 ml) was added lM solution of tetrabutylammonium fluoride in tetrahydrofuran (32.3 ml) at 0° C. After stirring at room temperature for 1 hour, the reaction mixture was poured into a mixture of ethyl acetate (200 ml) and water (100 ml). The aqueous layer was separated and extracted with ethyl acetate. The combined organic layer was washed twice with 1N hydrochloric acid (25 ml) and then with saturated aqueous sodium bicarbonate, water and brine successively, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel (100 ml) eluting with a mixture of n-hexane and ethyl acetate (1:1-1:2 V/V) to give (2S,4R)-1-allyloxycarbonyl-4-hydroxy-2-(2-methyl-3-oxo-1-butenyl)pyrrolidine (5.65 g).

1. customThe aqueous layer was separated
2. extractionextracted with ethyl acetate
3. washThe combined organic layer was washed twice with 1N hydrochloric acid (25 ml)
4. dry with materialwith saturated aqueous sodium bicarbonate, water and brine successively, dried over magnesium sulfate
5. customevaporated
6. customThe residue was chromatographed on silica gel (100 ml)
7. washeluting with a mixture of n-hexane and ethyl acetate (1:1-1:2 V/V)

ORD record

ord-76aab21f18d14c0db7a8409472985ffd

Source dataset

uspto-grants-1990_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04923857