tert-Butyl 4-oxopiperidine-1-carboxylate → HCID 66864309, 화합물

HRID 2093094

반응식

HRID 2093094 반응식
[C:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C([N-:18]C(C)C)(C)C.[Li+].[C:23]([O:28][CH2:29][CH2:30]Br)(=[O:27])[C:24]([CH3:26])=O>C1COCC1>[NH:18]1[C:11]2[CH2:12][CH2:13][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9][C:10]=2[CH:26]=[C:24]1[C:23]([O:28][CH2:29][CH3:30])=[O:27]

참가 물질

5

반응물 3

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 2724682Lithium diisopropylamideHCID 86587973Bromoethyl pyruvate

생성물 1

HCID 66864309HCID 66864309, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of N-boc-4-piperidone (1 eq.) and lithium di-isopropyl amide (1 eq.) in THF was stirred at −78° C. and for 2 hrs. A bromoethyl pyruvate (1.2 eq.) was added to above reaction mixture and stirred for 30 min. Reaction mixture was then quenched with ammonia solution and then extracted with ethyl acetate, dried over sodium sulphate and concentrated to dryness. The residue was then dissolved in dichoromethane and was added silica (100-200 mesh), stirred for overnight at room temperature. Crude was then purified by silica gel column chromatography to yield 5-tert-butyl 2-ethyl 1,4,6,7-tetrahydro-5H-pyrrolo[3,2-c]pyridine-2,5-dicarboxylate.

후처리

  1. customReaction mixture
  2. customwas then quenched with ammonia solution
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated to dryness
  6. dissolutionThe residue was then dissolved in dichoromethane
  7. additionwas added silica (100-200 mesh)
  8. stirringstirred for overnight at room temperature
  9. customCrude was then purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-6f708db8a9684e74b0489fe18c279fe5
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08440830B2

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