Ammonium Chloride → Ethyl 1-benzyl-5,5-difluoro-4-hydroxy-1,2,5,6-tetrahydropyridine-3-carboxylate

HRID 2206262노트

반응식

HRID 2206262 반응식
[CH2:1]([N:8]([CH2:16][C:17]([F:24])([F:23])[C:18]([O:20]CC)=O)[CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N-]C(C)C)(C)C.[Li+].[Cl-].[NH4+]>C1COCC1>[CH2:1]([N:8]1[CH2:16][C:17]([F:23])([F:24])[C:18]([OH:20])=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 59442745Ethyl 3-(benzyl(3-ethoxy-3-oxopropyl)amino)-2,2-difluoropropanoate

생성물 1

HCID 67343743Ethyl 1-benzyl-5,5-difluoro-4-hydroxy-1,2,5,6-tetrahydropyridine-3-carboxylate수율 126.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of ethyl N-benzyl-N-(3-ethoxy-2,2-difluoro-3-oxopropyl)-β-alaninate (25.0 g) in anhydrous THF (200 mL) was added dropwise lithium diisopropylamide (2M, 72.8 mL) at −78° C. The reaction mixture was stirred at room temperature for 2 hr, and added to saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound (27.4 g).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-f263252858d04d3fae7b487e51cbd375
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09371320B2

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