1-Pyrrolidinecarboxylic acid, 2-oxo-, 1,1-dimethylethyl ester → tert-butyl N-[4-(3-fluorophenyl)-4-oxobutyl]carbamate
反応式
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[F:14][C:15]1[CH:16]=[C:17]([Mg]Br)[CH:18]=[CH:19][CH:20]=1>C1COCC1>[F:14][C:15]1[CH:20]=[C:19]([C:2](=[O:1])[CH2:6][CH2:5][CH2:4][NH:3][C:7](=[O:8])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH:18]=[CH:17][CH:16]=1参加物
4
反応条件
- 温度
- -78 °C
実験手順
In a round-bottomed flask was charged tert-butyl 2-oxopyrrolidine-1-carboxylate (2.2 g, 11.9 mmol) and THF (25 mL). The mixture was cooled down to −78° C. first, followed by slow addition of (3-fluorophenyl)magnesium bromide (17.8 mL, 17.8 mmol, 1.0 M solution in THF) over 15 minutes. The mixture was stirred for 3 hours, during which time the bath temperature rose from −78° C. to −10° C. The reaction was quenched by drop-wise addition of 1N HCl (2 mL) and warmed up to ambient temperature, followed by addition of EtOAc and water. After separating the organic layer, the aqueous layer was extracted with EtOAc three times. The combined organic layers was dried over Na2SO4 and concentrated to yield the product as a clear oil.