Sodium Bicarbonate → 3-[4-Hydroxy-4-[(2-fluorophenyl)ethynyl)piperidino]methyl-1H-pyridin-2-one

HRID 890105ノート

反応式

HRID 890105 の反応式
Cl.[OH:2][C:3]1([C:9]#[C:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[O:18]=[C:19]1[C:24]([CH:25]=O)=[CH:23][CH:22]=[CH:21][NH:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.ClCCl>[OH:2][C:3]1([C:9]#[C:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])[CH2:4][CH2:5][N:6]([CH2:25][C:24]2[C:19](=[O:18])[NH:20][CH:21]=[CH:22][CH:23]=2)[CH2:7][CH2:8]1

参加物

7

反応物 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 70621962-Oxo-1,2-dihydropyridine-3-carbaldehydeHCID 222484404-Hydroxy-4-[(2-fluorophenyl)ethynyl]piperidine hydrochloride

生成物 1

HCID 222484353-[4-Hydroxy-4-[(2-fluorophenyl)ethynyl)piperidino]methyl-1H-pyridin-2-one収率 10%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

After then adding 253 mg of the 4-hydroxy-4-[(2-fluorophenyl)ethynyl]piperidine hydrochloride to 10 ml of dichloromethane, 158 mg of 2-oxo-1,2-dihydropyridine-3-carboxaldehyde was added and the mixture was stirred for 10 minutes at room temperature. Next, 315 mg of sodium triacetoxyborohydride was added and the mixture was stirred overnight at room temperature. Saturated aqueous sodium bicarbonate solution was added to the reaction mixture and extraction was performed with ethyl acetate. After drying the organic layer over magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by NH silica gel column chromatography to obtain the title compound (32 mg, 10% yield).

後処理

  1. additionwas added
  2. stirringthe mixture was stirred overnight at room temperature
  3. dry with materialAfter drying the organic layer over magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by NH silica gel column chromatography

出典と根拠

ORDレコード
ord-8f491786983e41c1a371fba2c8e6541b
出典データセット
uspto-grants-2006_02
特許番号
US06995144B2

反応ノート

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