tert-Butyl 4-oxopiperidine-1-carboxylate → HCID 66864309、化合物

HRID 2093094

反応式

HRID 2093094 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 66864309HCID 66864309、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6f708db8a9684e74b0489fe18c279fe5
出典データセット
uspto-grants-2013_05
特許番号
US08440830B2

関連ノート

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