反応 #40645
ord-5149e481278741f7a4613a29de63943b
反応方程式
反応条件
後処理
- 1温度cooled to −78° C.
- 2温度to warm to rt
- 3抽出the aqueous layer extracted with another portion of diethylether
- 4抽出extracted with dichloromethane (3×100 mL)
- 5乾燥The combined extracts were dried over Na2SO4
- 6ろ過filtered
- 7濃縮concentrated in vacuo
実験手順
n-Butyllithium (1.6 M in hexane, 8.8 mL, 14.0 mmol) was added dropwise under stirring over 5 min to a cooled solution of N,N-diisopropylamine (2.0 mL, 14.0 mmol) in THF (10 mL) at −40° C. The solution was warmed to 0° C. and a solution of 3-(4-fluoro-phenyl)propionic acid (1.18 g, 7.0 mmol) in THF (8 mL) was added. The mixture was stirred for 30 min at rt, cooled to −78° C. and N-BOC-4-piperidone (1.68 g, 8.4 mmol) in THF (7 mL) added dropwise over 15 min. The solution was allowed to warm to rt and poured into a stirred mixture of diethylether (100 mL) and water (50 mL). The organic layer was discarded, the aqueous layer extracted with another portion of diethylether. The aqueous layer was acidified with 2 M aq. HCl to pH 3.5 and extracted with dichloromethane (3×100 mL). The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo, giving 69NLS56 as a yellow solid, which is used without further purification.