Sodium → 2-Butyl-3-oxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile

HRID 489289노트

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HRID 489289 반응식
[CH2:1]([N:5]1[C:14](=[O:15])[C:13]([C:16]#[N:17])=[C:12]2[C:7]([C:8](=O)[CH2:9][CH2:10][CH2:11]2)=[CH:6]1)[CH2:2][CH2:3][CH3:4].[Na]>C1COCC1>[CH2:1]([N:5]1[C:14](=[O:15])[C:13]([C:16]#[N:17])=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][CH2:11]2)=[CH:6]1)[CH2:2][CH2:3][CH3:4]

참가 물질

4

반응물 2

HCID 5360545Sodium2회HCID 222664802-Butyl-3,8-dioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile

생성물 1

HCID 222664592-Butyl-3-oxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile수율 75%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

2-Butyl-3,8-dioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile (7-011) (100 mg, 0.41 mmol) was dissolved in THF (7 mL) and to the reaction mixture were added boron trifluoride diethyl ether complex (0.21 mL, 1.64 mmol) and sodium cyanoborohydried (90 mg, 1.44 mmol), and the reaction mixture was stirred at room temperature for 30 min. To the reaction mixture was added an saturated aqueous solution of sodium hydrogencarbaonate (30 mL) and the reaction mixture was extracted with ethyl acetate (60 mL), washed with brine (30 mL), dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (toluene/ethyl acetate) to give 2-butyl-3-oxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile (7-012) (70 mg, 75%) as a white solid.

후처리

  1. extractionthe reaction mixture was extracted with ethyl acetate (60 mL)
  2. washwashed with brine (30 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-b5cbd08b54124808baecc6ff7f3d1940
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06977266B2

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