(R)-tert-butyl 2-(2-oxoethyl)pyrrolidine-1-carboxylate → (2R)-tert-butyl 2-(2-(3-chloro-4-fluorophenyl)-2-hydroxyethyl)pyrrolidine-1-carboxylate
Reaktionsgleichung
[O:1]=[CH:2][CH2:3][C@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[Cl:16][C:17]1[CH:18]=[C:19]([Mg]Br)[CH:20]=[CH:21][C:22]=1[F:23]>C1COCC1>[Cl:16][C:17]1[CH:18]=[C:19]([CH:2]([OH:1])[CH2:3][C@H:4]2[CH2:8][CH2:7][CH2:6][N:5]2[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:20]=[CH:21][C:22]=1[F:23]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of (R)-tert-butyl 2-(2-oxoethyl)pyrrolidine-1-carboxylate (A. Furstner and J. W. L. Kennedy, Chem.—Eur. J. 2006 12(28):7398-7410) in THF cooled to −78° C. was added (3-chloro-4-fluorophenyl)magnesium bromide (0.720 mL, 0.360 mmol) and the reaction was warmed to RT for 1 h. The reaction was quenched with water and extracted with EtOAc. The organic layer was washed with water and brine, dried (Na2SO4), filtered and concentrated to afford an oil which was purified by SiO2 chromatography to afford 0.0745 g (72%) of (2R)-tert-butyl 2-(2-(3-chloro-4-fluorophenyl)-2-hydroxyethyl)pyrrolidine-1-carboxylate (301) as a clear oil.