تفاعل #45451

معادلة التفاعل

ammonium chloride

solution

tert-butyl (2S)-2-(2,2-dibromovinyl)pyrrolidine-1-carboxylate

sec-butyl lithium

→

desired product

tert-butyl (2S)-2-ethynylpyrrolidine-1-carboxylate

المذيبات

ether

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto warm to room temperature
2. 2
   استخلاصextracted
3. 3
   غسيلThe combined organic layers were washed with brine
4. 4
   تجفيفdried (MgSO4)
5. 5
   تركيزconcentrated

الإجراء التجريبي

A solution of Example 538A (6.11 g, 17.21 mmol) in THF (150 mL) at −78° C. was treated with sec-butyl lithium (24.6 mL, 34.41 mmol) dropwise via syringe and stirred for 30 minutes at −78° C. The solution was then treated with a saturated ammonium chloride solution (100 mL), allowed to warm to room temperature, diluted with ether and extracted. The combined organic layers were washed with brine, dried (MgSO4) and concentrated to provide the desired product in quantitative yield. MS (ESI(+)) m/e 196 (M+H)+.

المصدر