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

HRID 914896노트

반응식

HRID 914896 반응식
[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

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 6212Chloroform용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ff715508a90a4b64818b1402849e8a4d
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07265108B2

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