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 1M 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-3oxo-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-4dfda69937e54915ab05033755a2a419

Source dataset

uspto-grants-1992_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05081237