Potassium Permanganate → HCID 22958903, compound

HRID 1178881Notes

Reaction equation

HRID 1178881 reaction equation
[CH:1]([CH:3]1[CH2:9][CH:8]2[N:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]([CH2:6][CH2:7]2)[CH2:4]1)=[O:2].[O-:16][Mn](=O)(=O)=O.[K+]>CC(O)(C)C>[CH2:14]([O:13][C:11]([N:10]1[CH:8]2[CH2:7][CH2:6][CH:5]1[CH2:4][CH:3]([C:1]([OH:16])=[O:2])[CH2:9]2)=[O:12])[CH3:15]

Participants

4

Reactant 2

HCID 516875Potassium PermanganateHCID 58975238HCID 58975238, compound

Product 1

HCID 22958903HCID 22958903, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A solution of ethyl 3-formyl-8-azabicyclo[3.2.1]octane-8-carboxylate (1-3) (1.84 g, 8.71 mmol) in t-BuOH (50.0 mL) was diluted with an aqueous 5% NaH2PO4 solution (35.3 mL, 14.8 mmol, 0.42 N in water). With vigorous stirring, an aqueous 1.0 M KMnO4 solution (52.3 mL, 52.3 mmol) was added at room temperature. The mixture was stirred for 10 minutes and quenched with a saturated aqueous solution of Na2SO3. The resulting pH of the mixture was adjusted to 3 with cold (0° C.) dilute HCl to dissolve the colloidal MnO2. The mixture was then extracted with EtOAc and the combined organic layers were washed with brine, dried over anhydrous MgSO4, concentrated to give (1-4) as white solid.

Workup

  1. customquenched with a saturated aqueous solution of Na2SO3
  2. customwas adjusted to 3 with cold (0° C.) dilute HCl
  3. dissolutionto dissolve the colloidal MnO2
  4. extractionThe mixture was then extracted with EtOAc
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-956eb162e2464261812b76e3bbf20579
Source dataset
uspto-grants-2007_10
Patent number
US07276520B2

Reaction notes

Loading…