反应详情

A solution of (cis)-1-benzoyl-4-hydroxy-L-proline (7.074 gm, 30.1 mmole) in acetone was treated dropwise with 1,8-diazabicyclo[5.4.0]- undec-7-ene (5.4 ml, 36.1 mmole) while cooling with a water bath. After stirring under argon for 10 minutes, benzyl bromide (4.3 ml, 36.1 mmole) was added dropwise. After stirring for 3 hours at room temperature, an additional aliquot (0.25 ml) of benzyl bromide was added. The reaction was stirred overnight and the acetone removed in vacuo. The residue was partitioned between ethyl acetate and 1N HCl. The organic layer was washed with additional HCl, sodium bicarbonate solution, brine, and dried (sodium sulfate). Filtration, followed by concentration in vacuo afforded a solid which was recrystallized from ethyl acetate. The yield of the title compound was 8.77 gm (90%).

1. temperaturewhile cooling with a water bath
2. stirringAfter stirring for 3 hours at room temperature
3. stirringThe reaction was stirred overnight
4. customthe acetone removed in vacuo
5. customThe residue was partitioned between ethyl acetate and 1N HCl
6. washThe organic layer was washed with additional HCl, sodium bicarbonate solution, brine
7. dry with materialdried (sodium sulfate)
8. filtrationFiltration
9. concentrationfollowed by concentration in vacuo
10. customafforded a solid which
11. customwas recrystallized from ethyl acetate