Triacetoxyperiodinane → 2'-(4-Methoxybenzyloxy)-2,3,5,6-tetrahydro[1,3']bipyridinyl-4-one

HRID 632823Notes

Reaction equation

HRID 632823 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH3:23][O:24][C:25]1[CH:45]=[CH:44][C:28]([CH2:29][O:30][C:31]2[C:36]([N:37]3[CH2:42][CH2:41][CH:40]([OH:43])[CH2:39][CH2:38]3)=[CH:35][CH:34]=[CH:33][N:32]=2)=[CH:27][CH:26]=1>ClCCl>[CH3:23][O:24][C:25]1[CH:26]=[CH:27][C:28]([CH2:29][O:30][C:31]2[C:36]([N:37]3[CH2:42][CH2:41][C:40](=[O:43])[CH2:39][CH2:38]3)=[CH:35][CH:34]=[CH:33][N:32]=2)=[CH:44][CH:45]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 121249534HCID 121249534, compound

Product 1

HCID 1212495762'-(4-Methoxybenzyloxy)-2,3,5,6-tetrahydro[1,3']bipyridinyl-4-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of Dess-Martin periodinane (9.19 g, 21.67 mmol) in dichloromethane (95 ml) at room temperature was treated with a solution of 2′-(4-Methoxybenzyloxy)-3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl-4-ol (5.68 g, 18.06 mmol) in dichloromethane (60 ml) and the reaction mixture was stirred at room temperature (a mild exotherm was observed). After 1 hour, the reaction mixture was washed with sat'd Na2S2O3(aq.), sat'd NaHCO3(aq.), sat'd NaCl(aq.), dried over MgSO4, filtered, and concentrated. Elution through a flash column (silica gel 60, 230-400 mesh, 7:3 hexanes:EtOAc to 3:2 hexanes:EtOAc) gave the title compound as a yellow, viscous oil (4.01 g, 71%).

Workup

  1. washthe reaction mixture was washed with sat'd Na2S2O3(aq.), sat'd NaHCO3(aq.), sat'd NaCl(aq.)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washElution through a flash column (silica gel 60, 230-400 mesh, 7:3 hexanes:EtOAc to 3:2 hexanes:EtOAc)

Sources & evidence

ORD record
ord-ff31a3a2f4e9491095e7e82556fff353
Source dataset
uspto-grants-2016_04
Patent number
US09321766B1

Reaction notes

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