反应详情

To a stirred solution of (Benzhydrylidene-amino)-acetic acid tert-butyl ester (3.00 g; 10.1 mmol) in 60 mL of tetrahydrofuran under argon at −78° C. was added lithium diisopropylamide solution (11.5 mL; 1.5 M solution in cyclohexane) dropwise. After 30 minutes, a solution of cycloheptylmethyl iodide (Prepared in Step A; 3.83 g; 15.2 mmol) was added dropwise via syringe and the mixture allowed to warm to room temperature and stirred for 18 h. The mixture was quenched with saturated sodium bicarbonate solution and most of the tetrahydrofuran was removed in vacuo. The mixture was diluted with water and extracted with methylene chloride. The combined extracts were dried (sodium sulfate) filtered and concentrated in vacuo. The crude product was chromatographed (eluent:4% ethyl acetate/hexanes) to give 3.34 g (79%) of 2-(Benzhydrylidene-amino)-3-cyclooctyl-propionic acid tert-butyl ester as a pale yellow oil.

1. customThe mixture was quenched with saturated sodium bicarbonate solution and most of the tetrahydrofuran
2. customwas removed in vacuo
3. additionThe mixture was diluted with water
4. extractionextracted with methylene chloride
5. dry with materialThe combined extracts were dried (sodium sulfate)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe crude product was chromatographed (eluent:4% ethyl acetate/hexanes)