Potassium Permanganate → 4-Oxo-5-[2-(N-BOC-4-Piperidinyl)ethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

HRID 1741595Notes

Reaction equation

HRID 1741595 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][C:19]3[S:22][CH:23]=[CH:24][C:18]=3[CH2:17]2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[O-:25][Mn](=O)(=O)=O.[K+]>CC(C)=O>[O:25]=[C:17]1[C:18]2[CH:24]=[CH:23][S:22][C:19]=2[CH2:20][CH2:21][N:16]1[CH2:15][CH2:14][CH:11]1[CH2:12][CH2:13][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 516875Potassium PermanganateHCID 10498076HCID 10498076, compound

Product 1

HCID 105708044-Oxo-5-[2-(N-BOC-4-Piperidinyl)ethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2-3 (3.25 g, 0.0093 moles) in acetone (100 ml) was treated at room temperature with KMnO4 (2.93 g, 0.0185 moles) and the resulting mixture was stirred for 1 hour. The mixture was then filtered (silica gel pad), concentrated and the residue purified by flash chromatography on silica gel eluting with EtOAc (2)/hexanes (3) to give pure 2-4 as an oil.

Workup

  1. filtrationThe mixture was then filtered (silica gel pad)
  2. concentrationconcentrated
  3. customthe residue purified by flash chromatography on silica gel eluting with EtOAc (2)/hexanes (3)

Sources & evidence

ORD record
ord-de9dbb6db8a64df5ab7f52a6c0858068
Source dataset
uspto-grants-1994_08
Patent number
US05334596

Reaction notes

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