反応 #607492

反応方程式

137m

7,7-dimethyl-1-oxo-2,3,4,6,7,8-hexahydro-1H-pyrido[3,4-b]pyrrolizine-9-carboxylic acid

phenanthroline

quinoline

HCl

→

7,7-dimethyl-2,3,4,6,7,8-hexahydro-1H-pyrido[3,4-b]pyrrolizin-1-one

収率 61.0%

溶媒

NMP

Water

反応条件

後処理

1. 1
   その他The reaction mixture was microwaved at 200° C. for 3 h
2. 2
   抽出extracted with EA (50 mL×3)
3. 3
   乾燥The combined organic extracts were dried over anhydrous sodium sulfate
4. 4
   ろ過filtered
5. 5
   濃縮concentrated under reduced pressure
6. 6
   その他The residue was purified by silica gel chromatography (DCM/MeOH=10/1)

実験手順

A microwave vial was charged with 137m (900 mg, 3.63 mmol), Cu2O (26 mg, 0.18 mmol), phenanthroline (66 mg, 0.36 mmol), quinoline (3 g, 23 mmol) and NMP (8 mL). The reaction mixture was microwaved at 200° C. for 3 h. See FIG. 2. Water was added and the mixture was neutralized to pH 7 by addition of 1N HCl and extracted with EA (50 mL×3). The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (DCM/MeOH=10/1) to give 7,7-dimethyl-2,3,4,6,7,8-hexahydro-1H-pyrido[3,4-b]pyrrolizin-1-one 137n (450 mg, 61%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 6.18 (t, J=1.2 Hz, 1H), 5.16 (s, 1H), 3.57 (s, 4H), 2.76 (t, J=6.9 Hz, 2H), 2.64 (d, J=1.1 Hz, 2H), 1.25 (s, 6H); MS-ESI [M+H]+=205.1.

出典