Lithium Hydroxide → (3S,4R)-4-(2,4-Difluorophenyl)-1-isopropylpyrrolidine-3-carboxylic acid
Reaktionsgleichung
[OH-].[Li+].[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[C@@H:11]1[CH2:15][N:14]([CH:16]([CH3:18])[CH3:17])[CH2:13][C@H:12]1[C:19]([O:21]C)=[O:20]>O1CCCC1>[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[C@@H:11]1[CH2:15][N:14]([CH:16]([CH3:17])[CH3:18])[CH2:13][C@H:12]1[C:19]([OH:21])=[O:20]Komponenten
4
Versuchsvorschrift
Lithium hydroxide (171 mg, 7.14 mmol) was added to a solution of methyl (3S,4R)-4-(2,4-difluorophenyl)-1-isopropylpyrrolidine-3-carboxylate, from preparation 32 (1.01 g, 3.59 mmol) in tetrahydrofuran (10 mL) at room temperature. The reaction mixture was stirred for 3 hours and the solvent was removed in vacuo. The residue was dissolved in water (20 mL) and washed with ethyl acetate (2×20 mL). The phases were separated and the aqueous phase was acidified with 2M aqueous hydrochloric acid solution (3.59 mL) and extracted with ethyl acetate (20 mL). The organic extracts were combined, dried over magnesium sulfate and concentrated in vacuo to afford the desired product as a foam, 686 mg (71%).