Sodium Carbonate → 1-[1-[1-(3-Methoxy-2-pyrazinyl)ethyl]piperidin-4-yl]-2-(2-fluorophenyl)ethanone

HRID 606249ノート

反応式

HRID 606249 の反応式
Cl.[F: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]([C:21]1[C:26]([O:27][CH3:28])=[N:25][CH:24]=[CH:23][N:22]=1)(=O)[CH3:19].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4].C(OCC)(=O)C.C(N(CC)CC)C>[CH3:28][O:27][C:26]1[C:21]([CH:18]([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[F:2])[CH2:17][CH2:16]2)[CH3:19])=[N:22][CH:23]=[CH:24][N:25]=1

参加物

9

反応物 4

HCID 10340Sodium CarbonateHCID 5398321-(3-Methoxy-2-pyrazinyl)ethanoneHCID 5049666Sodium triacetoxyborohydrideHCID 222481242-(2-Fluorophenyl)-1-(piperidin-4-yl)ethanone hydrochloride

生成物 1

HCID 222484241-[1-[1-(3-Methoxy-2-pyrazinyl)ethyl]piperidin-4-yl]-2-(2-fluorophenyl)ethanone収率 9.5%

試薬・触媒・溶媒 4

HCID 11026Titanium isopropoxide触媒HCID 702Ethanol溶媒2 回HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

After dissolving 1.012 g of triethylamine in 10 ml of ethanol, 2.575 g of 2-(2-fluorophenyl)-1-(piperidin-4-yl)ethanone hydrochloride, 10 ml of ethanol, 2.951 ml of titanium (IV) tetraisopropoxide and 760 mg of 2-acetyl-3-methoxypyrazine were added in that order and the mixture was stirred for 5 hours and 20 minutes at room temperature. Next, 1.59 g of sodium triacetoxyborohydride was added to the reaction mixture and the mixture was stirred overnight at room temperature. A sodium carbonate solution and ethyl acetate were added to the reaction mixture and the mixture was filtered with celite. The filtrate was extracted with ethyl acetate, and the extract was washed with water and saturated brine and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and then the residue was dissolved in ethyl acetate and filtered with silica gel. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (169 mg, 9% yield).

後処理

  1. additionwere added in that order
  2. stirringthe mixture was stirred overnight at room temperature
  3. filtrationthe mixture was filtered with celite
  4. extractionThe filtrate was extracted with ethyl acetate
  5. washthe extract was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. dissolutionthe residue was dissolved in ethyl acetate
  9. filtrationfiltered with silica gel
  10. distillationThe solvent was distilled off under reduced pressure
  11. customthe residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-96b71c48c6334d8183e248a605d6e34a
出典データセット
uspto-grants-2011_03
特許番号
US07915274B2

反応ノート

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