反応 #332611
ord-b080f6c617d74125a6d08c595459593d
反応方程式
反応物
試薬
反応条件
後処理
- 1温度then cooled again to −78° C
- 2その他at −78° C.
- 3その他at −78° C
- 4温度Allowed the solution to warm to −50° C.
- 5その他quenched with saturated ammonium chloride solution
- 6抽出Extracted mixture with ethyl acetate
- 7洗浄washed
- 8その他resulting organics with brine
- 9ろ過Dried organics over sodium sulfate, filtered
- 10その他evacuated filtrate under vacuum
- 11その他to give crude yellow oil
- 12その他The crude oil was purified on silica using 10-30% acetone in n-hexane as eluant
実験手順
Diisopropylamine (0.925 mL, 6.55 mmol) was added dropwise to a stirring solution of 2.5M n-butyllithium in hexane (2.495 mL, 6.24 mmol) in THF (10 mL) at −78° C. Allowed solution to warm to 0° C. for 10 minutes then cooled again to −78° C. Cannulated the prepared LDA at −78° C. into (2R,6S)-4-(2-((tert-butyldiphenylsilyloxy)methyl)-4-chloro-5-fluoropyridin-3-yl)-2,6-dimethylmorpholine (Intermediate 45, 1.6 g, 3.12 mmol) in THF (10 mL) at −78° C. Allowed the dark solution to stir for 20 minutes and then cannulated into a stirring solution of N-methoxy-N-methylpicolinamide (1.05 g, 6.24 mmol) in THF (10 mL) at −78° C. Allowed the solution to warm to −50° C. and then quenched with saturated ammonium chloride solution. Extracted mixture with ethyl acetate and washed resulting organics with brine. Dried organics over sodium sulfate, filtered, and evacuated filtrate under vacuum to give crude yellow oil. The crude oil was purified on silica using 10-30% acetone in n-hexane as eluant to give 1.3 g (67%) of the title compound as oil.