Lithium Hydroxide → HCID 59588989, compound

Temperature

0 °C

A mixture of triethyl 2-fluoro-2-phosphonoacetate (1.07 mL, 5.2 mmol), tert-butyl (2-oxopropyl)carbamate (0.865 g, 5.0 mmol) and lithium hydroxide (0.21 g, 5.0 mmol) in THF (15 mL) was at room temperature for 16 hours. The mixture was cooled to 0° C. and lithium borohydride (0.22 g, 10.0 mmol) was added in portions. Stirring was continued at 0° C. for 1 hour and at room temperature for 2 hours. Saturated ammonium chloride solution (25 mL) was added to the mixture and the organic layer extracted with ethyl acetate (50 mL) and washed with brine (20 mL), dried over MgSO4, filtered and the solvent removed under reduced pressure to afford the crude product as a clear oil (0.90 g). Purification by flash chromatography eluting in 20% EtOAc in n-hexane afforded tert-butyl [(2E)-3-fluoro-4-hydroxy-2-methylbut-2-en-1-yl]carbamate (0.33 g, 30%) as white solid. 1H-NMR (400 MHz, CDCl3): δppm: 1.42 (9H, s), 1.68 (3H, d, J 3.2 Hz), 3.67 (2H, dd, J 6.4, 1.2 Hz), 3.80 (1H, t, J 6.4 Hz), 4.26 (2H, dd, J 24.8, 6.4 Hz), 4.98 (1H, brs).

1. waitwas continued at 0° C. for 1 hour and at room temperature for 2 hours
2. extractionthe organic layer extracted with ethyl acetate (50 mL)
3. washwashed with brine (20 mL)
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. customthe solvent removed under reduced pressure
7. customto afford the crude product as a clear oil (0.90 g)
8. customPurification by flash chromatography
9. washeluting in 20% EtOAc in n-hexane

ORD record

ord-c1fd2024a66a4ba0a7c3d570abfa3ea5

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08426587B2