HCID 67382347, compound → HCID 57656622, compound

HRID 911617Notes

Reaction equation

HRID 911617 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([CH:16]([OH:24])[CH2:17][C:18]([CH2:22]C)([CH2:20]C)[CH3:19])=[N:14][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>O1CCOCC1.[O-2].[O-2].[Mn+4]>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16](=[O:24])[CH2:17][C:18]([CH3:22])([CH3:20])[CH3:19])=[N:14][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 67382347HCID 67382347, compound

Product 1

HCID 57656622HCID 57656622, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

Add manganese dioxide (472 mg, 5.429 mmol) to a solution of 5-tert-butoxycarbonylaminomethyl-2-(1-hydroxy-3,3-diethyl-butyl)-pyridine (118 mg, 0.383 mmol) in anhydrous 1,4-dioxane (5 mL) at room temperature. Heat the reaction mixture at 70° C. overnight. Filter the reaction mixture over Celite® and concentrate in vacuo to obtain the desired intermediate (104 mg, 89%).

Workup

  1. filtrationFilter the reaction mixture over Celite®
  2. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-ccd3ac01e8d746a7abd2ca29ad589fd2
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

Loading…