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

HRID 632830Notes

Reaction equation

HRID 632830 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:46]=[CH:45][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)=[C:35]([CH3:44])[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)=[C:35]([CH3:44])[CH:34]=[CH:33][N:32]=2)=[CH:45][CH:46]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 1212495502'-(4-Methoxybenzyloxy)-4'-methyl-3,4,5,6-tetrahydro-2H-[1,3']bipyridinyl-4-ol

Product 1

HCID 1212495972'-(4-Methoxybenzyloxy)-4'-methyl-2,3,5,6-tetrahydro[1,3']bipyridinyl-4-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of Dess-Martin periodinane (11.61 g, 27.37 mmol) in dichloromethane (122 ml) at room temperature was treated with a solution of 2′-(4-Methoxybenzyloxy)-4′-methyl-3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl-4-ol (7.49 g, 22.81 mmol) in dichloromethane (81 ml) and the reaction mixture was stirred at room temperature. After 1 hour, the reaction mixture was washed with sat'd Na2S2O3(aq.), sat'd NaHCO3(aq.), and sat'd NaCl(aq.), dried over MgSO4, filtered, and concentrated. Elution through a flash column (silica gel 60, 230-400 mesh, 3:2 hexanes:EtOAc) gave the title compound as an off-white, crystalline solid (6.40 g, 86%).

Workup

  1. washthe reaction mixture was washed with sat'd Na2S2O3(aq.), sat'd NaHCO3(aq.), and 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, 3:2 hexanes:EtOAc)

Sources & evidence

ORD record
ord-421c194aebe9495c9b1eb5c4c3bf6256
Source dataset
uspto-grants-2016_04
Patent number
US09321766B1

Reaction notes

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