تفاعل #607492

معادلة التفاعل

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

المردود 61.0%

المذيبات

NMP

Water

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction mixture was microwaved at 200° C. for 3 h
2. 2
   استخلاصextracted with EA (50 mL×3)
3. 3
   تجفيفThe combined organic extracts were dried over anhydrous sodium sulfate
4. 4
   ترشيحfiltered
5. 5
   تركيزconcentrated under reduced pressure
6. 6
   أخرىThe residue was purified by silica gel chromatography (DCM/MeOH=10/1)

الإجراء التجريبي

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.

المصدر