Potassium Permanganate → Ethyl 6'-bromo-1'-(1,1-dimethylethylsulfinamido)-4-methoxy-1',3'-dihydrospiro[cyclohexane-1,2'-indene]-1'-carboxylate

HRID 1503435Notes

Reaction equation

HRID 1503435 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:27][CH2:26][CH:25]([O:28][CH3:29])[CH2:24][CH2:23]3)[C:8]2([NH:16][S:17]([C:19]([CH3:22])([CH3:21])[CH3:20])=[O:18])[C:11]([O:13][CH2:14][CH3:15])=C)=[CH:4][CH:3]=1.[O-:30][Mn](=O)(=O)=O.[K+]>CC(C)=O>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:27][CH2:26][CH:25]([O:28][CH3:29])[CH2:24][CH2:23]3)[C:8]2([NH:16][S:17]([C:19]([CH3:21])([CH3:22])[CH3:20])=[O:18])[C:11]([O:13][CH2:14][CH3:15])=[O:30])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 516875Potassium Permanganate2×HCID 58198087N-(6'-bromo-1'-(1-ethoxyvinyl)-4-methoxy-1',3'-dihydrospiro[cyclohexane-1,2'-indene]-1'-yl)-2-methylpropane-2-sulfinamide

Product 1

HCID 58197767Ethyl 6'-bromo-1'-(1,1-dimethylethylsulfinamido)-4-methoxy-1',3'-dihydrospiro[cyclohexane-1,2'-indene]-1'-carboxylateYield 31%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of N-(6′-bromo-1′-(1-ethoxyvinyl)-4-methoxy-1′,3′-dihydrospiro[cyclohexane-1,2′-indene]-1′-yl)-2-methylpropane-2-sulfinamide (5) (200 mg, 0.48 mmol) in acetone (15 mL) at room temperature (23° C.) was added a KMnO4 solution (5.8 mL, prepared by dissolving 9.5 g of KMnO4 in 100 mL of H2O). The mixture was stirred room temperature for 16 h. Another portion of KMnO4 solution (2.2 mL) was added and stirred another 12 h. The reaction was quenched with 5% NaHSO3, stirring until colorless clear solution achieved before combined. The combined organic phases were extracted with EA 2 times, washed with brine, dried over Na2SO4, evaporated after filtration. The residue was purified by flash chromatography on silica gel eluted with EA in hexane (0-60%) to afford the desired amino ester (6) (62.8 mg, 31%). MS ESI+ve m/z 486 (M+H)30.

Workup

  1. stirringstirred another 12 h
  2. customThe reaction was quenched with 5% NaHSO3
  3. stirringstirring until colorless clear solution
  4. extractionThe combined organic phases were extracted with EA 2 times
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. filtrationafter filtration
  9. customThe residue was purified by flash chromatography on silica gel
  10. washeluted with EA in hexane (0-60%)

Sources & evidence

ORD record
ord-6cba725a56ee47a298d2e22768dee823
Source dataset
uspto-grants-2015_12
Patent number
US09212153B2

Reaction notes

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