4-Methyloxybenzyl chloride → 1-Tert-butyl 3-ethyl 3-(4-methylbenzyl)piperidine-1,3-dicarboxylate

HRID 1860641노트

반응식

HRID 1860641 반응식
[N:1]1([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5][CH2:4][CH:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:2]1.[CH:19](NC(C)C)(C)C.[Li].CO[C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Cl)=[CH:31][CH:30]=1>C1COCC1>[CH3:19][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][C:3]2([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:4][CH2:5][CH2:6][N:1]([C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])[CH2:2]2)=[CH:31][CH:30]=1

참가 물질

5

반응물 3

HCID 699934-Methyloxybenzyl chlorideHCID 3577271-Tert-butyl 3-ethyl piperidine-1,3-dicarboxylateHCID 45051747Lithium diisopropylamine

생성물 1

HCID 229784271-Tert-butyl 3-ethyl 3-(4-methylbenzyl)piperidine-1,3-dicarboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
0 °C

실험 절차

A solution of the product from STEP 1 (5.0 g, 19.5 mmol) in 20 ml THF was added to a solution of lithium diisopropylamine (11.7 ml, 23.4 mmol, 2M solution) in 25 ml THF dropwise at −20° C. The resulting mixture was stirred at 0° C. for 15 min and allowed to warm to room temperature. After 1 h, the reaction was cooled to −20° C. and treated, dropwise, with a solution of 4-methoxy-benzyl chloride (3.1 g, 19.5 mmol) in 20 ml THF. The resulting mixture was stirred at −10° C. for 1 h, and warmed to 35° C. After 1 h, the reaction was quenched with 25 ml saturated aqueous NH4Cl solution. The product was extracted with ethyl acetate (2×100 ml). The aqueous layer was extracted with ethyl acetate. The combined layers were were washed with H2O, brine, and then dried with Na2SO4, and concentrated. The residue was purified by chromatography (on silica gel, ethyl acetate/hexane=1/4) to yield a viscous oil in 5.2 g. The 1H NMR spectrum of the product was consistent for the proposed structure.

후처리

  1. temperatureto warm to room temperature
  2. waitAfter 1 h
  3. temperaturethe reaction was cooled to −20° C.
  4. additiontreated
  5. stirringThe resulting mixture was stirred at −10° C. for 1 h
  6. temperaturewarmed to 35° C
  7. waitAfter 1 h
  8. customthe reaction was quenched with 25 ml saturated aqueous NH4Cl solution
  9. extractionThe product was extracted with ethyl acetate (2×100 ml)
  10. extractionThe aqueous layer was extracted with ethyl acetate
  11. washThe combined layers were were washed with H2O, brine
  12. dry with materialdried with Na2SO4
  13. concentrationconcentrated
  14. customThe residue was purified by chromatography (on silica gel, ethyl acetate/hexane=1/4)
  15. customto yield a viscous oil in 5.2 g

출처 및 근거

ORD 기록
ord-c7a21b5a1dbc47da869f2b4224da2793
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06531494B1

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