반응 #303254

반응 방정식

2-bromo-N,N-dimethylethanamine

1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate

LDA

→

title compound

수율 50.0%

1-tert-butyl 4-ethyl 4-(2-(dimethylamino)ethyl)piperidine-1,4-dicarboxylate

수율 50.0%

용매

THF

THF

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction was stirred for 30 min at −78° C.
2. 2
   workup.STIRRINGstirred for 2 hours
3. 3
   기타quenched with sat. aq. NaHCO3
4. 4
   workup.ADDITIONdiluted with EtOAc
5. 5
   세척washed with sat. aq. NaHCO3 and brine (with back extraction)
6. 6
   건조dried over MgSO4
7. 7
   농축concentrated under vacuum
8. 8
   기타The residue was purified by flash chromatography (40 g SiO2, 0-15% MeOH:CH2Cl2)

실험 절차

To a solution of 1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate (514 mg, 2 mmol) in THF (10 mL) at −78° C. was added dropwise LDA (1.5 M in cyclohexane, 2 mL, 3 mmol). After stirring for 30 minutes, 2-bromo-N,N-dimethylethanamine (370 mg, 2.4 mmol) in THF (3 mL) was added. The reaction was stirred for 30 min at −78° C., then allowed to warm to room temperature, stirred for 2 hours, then quenched with sat. aq. NaHCO3, diluted with EtOAc, washed with sat. aq. NaHCO3 and brine (with back extraction), dried over MgSO4, and concentrated under vacuum. The residue was purified by flash chromatography (40 g SiO2, 0-15% MeOH:CH2Cl2) to give the title compound (328 mg, 1.0 mmol, 50%) as a yellow oil. MS (ES+) [M+H]+=329.

출처