تفاعل #40527

معادلة التفاعل

4-Oxo-piperidine-1-carboxylic acid tert-butyl ester

tetrahydrofuran

Sodium hydride

Methyl iodide

→

3,3-dimethyl-4-oxo-piperidine-1-carboxylic acid tert-butyl ester

المردود 32.0%

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto warm to room temperature over several hours
2. 2
   workup.STIRRINGStirring
3. 3
   workup.WAITcontinued over night
4. 4
   أخرى(12 h)
5. 5
   تركيزThe light orange mixture was concentrated under reduced pressure
6. 6
   أخرىThe residue was partitioned between ether and water
7. 7
   استخلاصThe aqueous phase was back-extracted with additional ether
8. 8
   غسيلThe combined extracts were washed with water and brine
9. 9
   تجفيفdried over sodium sulfate
10. 10
    ترشيحfiltered
11. 11
    تركيزconcentrated to a pale yellow solid
12. 12
    أخرىThe solid was triturated with 4% ethyl acetate in hexanes (50 mL)

الإجراء التجريبي

4-Oxo-piperidine-1-carboxylic acid tert-butyl ester (5 g, 25 mmol) was dissolved in tetrahydrofuran (100 mL) and the resulting solution was cooled to 0° C. Sodium hydride (60% in mineral oil, 2.10 g, 53 mmol) was added to the cooled solution in a single portion, and the resulting cloudy mixture was allowed to stir 10 min. Methyl iodide was subsequently added and the mixture was allowed to warm to room temperature over several hours. Stirring continued over night (12 h). The light orange mixture was concentrated under reduced pressure. The residue was partitioned between ether and water. The aqueous phase was back-extracted with additional ether. The combined extracts were washed with water and brine, dried over sodium sulfate, filtered and concentrated to a pale yellow solid. The solid was triturated with 4% ethyl acetate in hexanes (50 mL) to afford 3,3-dimethyl-4-oxo-piperidine-1-carboxylic acid tert-butyl ester as a cream-colored solid (1.8 g, 32%).

المصدر