Sodium Hydroxide → 1-[1-(3-tert-Butoxy-2-pyrazinylmethyl)piperidin-4-yl]-2-(2-methylphenyl)ethanone

HRID 890080노트

반응식

HRID 890080 반응식
Cl.[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)=[O:11].[C:18]([O:22][C:23]1[C:24]([CH:29]=O)=[N:25][CH:26]=[CH:27][N:28]=1)([CH3:21])([CH3:20])[CH3:19].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCl>[C:18]([O:22][C:23]1[C:24]([CH2:29][N:15]2[CH2:14][CH2:13][CH:12]([C:10](=[O:11])[CH2:9][C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[CH3:2])[CH2:17][CH2:16]2)=[N:25][CH:26]=[CH:27][N:28]=1)([CH3:21])([CH3:20])[CH3:19]

참가 물질

6

반응물 4

HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 222482803-(tert-Butoxy)pyrazine-2-carbaldehydeHCID 222484752-(2-Methylphenyl)-1-(piperidin-4-yl)ethanone hydrochloride

생성물 1

HCID 222479841-[1-(3-tert-Butoxy-2-pyrazinylmethyl)piperidin-4-yl]-2-(2-methylphenyl)ethanone수율 68%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

After suspending 150 mg of 2-(2-methylphenyl)-1-(piperidin-4-yl)ethanone hydrochloride in 3 ml of dichloromethane, 128 mg of 3-tert-butoxypyrazine-2-carboxaldehyde and 188 mg of sodium triacetoxyborohydride were added while stirring on ice, and the stirring was continued overnight at room temperature. A 1N sodium hydroxide solution was added to the reaction mixture to render it alkaline, and then extraction was performed with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by NH silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (153 mg, 68% yield).

후처리

  1. additionwere added
  2. extractionextraction
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by NH silica gel column chromatography (solvent: n-hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-784ccc0f228146af8ccbb1e86266190f
출처 데이터셋
uspto-grants-2006_02
특허 번호
US06995144B2

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