Reaktion #45451

Reaktionsgleichung

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

Lösungsmittel

ether

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to room temperature
2. 2
   Extraktionextracted
3. 3
   WaschenThe combined organic layers were washed with brine
4. 4
   Trocknendried (MgSO4)
5. 5
   Einengenconcentrated

Vorschrift

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)+.

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