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

HRID 914896Notes

Reaction equation

HRID 914896 reaction equation
[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

Participants

9

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-ff715508a90a4b64818b1402849e8a4d
Source dataset
uspto-grants-2007_09
Patent number
US07265108B2

Reaction notes

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