Potassium Permanganate → HCID 67467458, compound

HRID 1908185Notes

Reaction equation

HRID 1908185 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:28]3[C:29]([CH:32]=[O:33])=[CH:30][CH:31]=[C:27]3[C:8]3([CH2:13][CH2:12][N:11]([C:14](=[O:26])[C:15]4[CH:20]=[CH:19][C:18]([O:21][CH:22]([CH3:24])[CH3:23])=[C:17]([CH3:25])[CH:16]=4)[CH2:10][CH2:9]3)[O:7][C:6]=2[CH:34]=1.[Mn]([O-])(=O)(=O)=[O:36].[K+]>CC(C)=O.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:28]3[C:29]([C:32]([OH:36])=[O:33])=[CH:30][CH:31]=[C:27]3[C:8]3([CH2:13][CH2:12][N:11]([C:14](=[O:26])[C:15]4[CH:20]=[CH:19][C:18]([O:21][CH:22]([CH3:24])[CH3:23])=[C:17]([CH3:25])[CH:16]=4)[CH2:10][CH2:9]3)[O:7][C:6]=2[CH:34]=1

Participants

5

Reactant 2

HCID 516875Potassium PermanganateHCID 86660260HCID 86660260, compound

Product 1

HCID 67467458HCID 67467458, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

To a solution of 7-chloro-1′-(4-isopropoxy-3-methylbenzoyl)spiro-[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1-carbaldehyde (130 mg, 0.27 mmol) in acetone (1.5 mL) was added a solution of potassium permanganate (43 mg, 16 μL, 0.27 mmol) in water (1.5 mL) and acetone (1.5 mL) dropwise at 0° C. The mixture was allowed to stir at room temperature for 2 h before it was concentrated onto Celite from methanol. Column chromatography on the residue (0-20% EtOAc/CH2Cl2) gave 7-chloro-1′-(4-isopropoxy-3-methylbenzoyl)spiro[benzo[b]-pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1-carboxylic acid (13%).

Workup

  1. concentrationwas concentrated onto Celite from methanol

Sources & evidence

ORD record
ord-6a4ce1cd199d4875be0ff71b4336cb3d
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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