반응 #1482115

반응 방정식

Et3N

alcohol

tert-Butyl 4-hydroxy-2-methyl-2-phenylpyrrolidine-1-carboxylate

Oxalyl chloride

DMSO

→

tert-Butyl 2-methyl-4-oxo-2-phenylpyrrolidine-1-carboxylate

용매

CH2Cl2

CH2Cl2

반응 조건

후처리

1. 1
   기타To a flame-dried flask equipped
2. 2
   기타The flask was immersed in a cooling bath at −78° C
3. 3
   workup.STIRRINGThe reaction was stirred 10 minutes at −78° C.
4. 4
   workup.STIRRINGThe resulting solution was stirred an additional 1 hour at −78° C.
5. 5
   세척Upon completion, the reaction solution was washed with 5% aq. NaHCO3
6. 6
   건조dried (MgSO4)
7. 7
   여과filtered
8. 8
   농축concentrated

실험 절차

To a flame-dried flask equipped with stir bar under nitrogen was charged anhydrous CH2Cl2 (5 mL). The flask was immersed in a cooling bath at −78° C. Oxalyl chloride (0.24 mL, 2.7 mmol) was added neat followed by DMSO (0.29 mL, 4.1 mmol) dropwise. The reaction was stirred 10 minutes at −78° C. prior to the addition of alcohol 20-5 (0.19 g, 0.7 mmol) in minimal CH2Cl2. The resulting solution was stirred an additional 1 hour at −78° C. prior to the addition of Et3N (0.76 mL, 5.4 mmol) neat and dropwise. The reaction warmed to 0° C. over 2 hour. Upon completion, the reaction solution was washed with 5% aq. NaHCO3, dried (MgSO4), filtered and concentrated. The residue was carried crude into the vinyl triflate formation: LRMS m/z (M-C(CH3)3+H) 220.1 found, 220.2 required.

출처