Sodium Bicarbonate → 3-[4-Hydroxy-4-(2-methyl-5-phenylpyrrol-1-yl)methyl-piperidino]methyl-1H-pyridin-2-one

HRID 914896ノート

反応式

HRID 914896 の反応式
[OH:1][C:2]1([CH2:8][N:9]2[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[O:21]=[C:22]1[C:27]([CH:28]=O)=[CH:26][CH:25]=[CH:24][NH:23]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCl.C(Cl)(Cl)Cl.C(OCC)(=O)C.C(O)(=O)C>[OH:1][C:2]1([CH2:8][N:9]2[C:10]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:11][CH:12]=[C:13]2[CH3:14])[CH2:7][CH2:6][N:5]([CH2:28][C:27]2[C:22](=[O:21])[NH:23][CH:24]=[CH:25][CH:26]=2)[CH2:4][CH2:3]1

参加物

9

反応物 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 70621962-Oxo-1,2-dihydropyridine-3-carbaldehydeHCID 222482014-Hydroxy-4-(2-phenyl-5-methylpyrrol-1-yl)methyl-piperidine

生成物 1

HCID 222485253-[4-Hydroxy-4-(2-methyl-5-phenylpyrrol-1-yl)methyl-piperidino]methyl-1H-pyridin-2-one収率 39%

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

After dissolving 35 mg of 4-hydroxy-4-(2-phenyl-5-methylpyrrol-1-yl)methyl-piperidine in 5 ml of dichloromethane, 16 mg of 2-oxo-1,2-dihydropyridine-3-carboxaldehyde and 0.02 ml of acetic acid were added and the mixture was stirred for 20 minutes at room temperature. Next, 41 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 and chloroform. After drying the organic layer over magnesium sulfate, the solvent was distilled off under reduced pressure. The obtained residue was purified by NH silica gel column chromatography to obtain the title compound (19 mg, 39% yield).

後処理

  1. additionwere 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 obtained residue was purified by NH silica gel column chromatography

出典と根拠

ORDレコード
ord-ff715508a90a4b64818b1402849e8a4d
出典データセット
uspto-grants-2007_09
特許番号
US07265108B2

反応ノート

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