Cesium fluoride → cis-3-[(R)-1-hydroxyethyl]-4-ethynyl-2-azetidinone

Temperature

60 °C

A cis/trans mixture (1.0 g) of 3-(1-hydroxyethyl)-4-trimethylsilylethynyl-2-azetidinone is dissolved in a mixture of tetrahydrofuran (10 ml) and methanol (5 ml), and a solution of cesium fluoride (0.2 g) in water (2 ml) is added to the solution. The mixture is stirred at 60° C. for an hour and concentrated under reduced pressure and the residue is extracted with ethyl acetate (20 ml) and tetrahydrofuran (20 ml). The extract is dried over magnesium sulfate, concentrated under reduced pressure and crystallized from ethyl acetate to give 0.18 g of cis-3-[(R)-1-hydroxyethyl]-4-ethynyl-2-azetidinone.

1. concentrationconcentrated under reduced pressure
2. extractionthe residue is extracted with ethyl acetate (20 ml) and tetrahydrofuran (20 ml)
3. dry with materialThe extract is dried over magnesium sulfate
4. concentrationconcentrated under reduced pressure
5. customcrystallized from ethyl acetate

ORD record

ord-751ea92dd0b44662bafb12c806b76a22

Source dataset

uspto-grants-1989_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04845210