반응 #42550

반응 방정식

tert-butyl (2R)-2-formylpyrrolidine-1-carboxylate

n-Butyl lithium

→

tert-butyl (2R)-2-vinylpyrrolidine-1-carboxylate

수율 63.4%

용매

THF

THF

반응 조건

후처리

1. 1
   workup.STIRRINGAfter stirring for 1 h
2. 2
   기타The cold bath was removed
3. 3
   workup.STIRRINGthe mixture stirred overnight at ambient temperature
4. 4
   기타The reaction mixture was then quenched with saturated NH4Cl
5. 5
   기타the phases were separated
6. 6
   세척the organic phase was washed with saturated NH4Cl, brine
7. 7
   건조dried over Na2SO4
8. 8
   여과filtered
9. 9
   농축concentrated
10. 10
    기타to give an orange oil
11. 11
    기타The oil was purified on a Biotage 40M column
12. 12
    세척eluting with heptane

실험 절차

n-Butyl lithium (1.6 M in hexanes)(27 mL, 43 mmol) was added to ice-cold hexamethyldisilazane (9.2 mL, 44 mmol) under a nitrogen atmosphere. The solution was stirred for 10 min and was then added to a suspension of methyl(triphenylphosphonium)bromide (15.5 g, 43 mmol) in 100 mL of THF at ambient temperature. After stirring for 1 h, the mixture was cooled to −78° C. and a solution of tert-butyl (2R)-2-formylpyrrolidine-1-carboxylate (7.9 g, 40 mmol) in 50 mL of THF was added. The cold bath was removed and the mixture stirred overnight at ambient temperature. The reaction mixture was then quenched with saturated NH4Cl, the phases were separated, and the organic phase was washed with saturated NH4Cl, brine, dried over Na2SO4, filtered, and concentrated to give an orange oil. The oil was purified on a Biotage 40M column eluting with heptane to give tert-butyl (2R)-2-vinylpyrrolidine-1-carboxylate (5.0 g).

출처