m-Chloroperbenzoic acid → HCID 15169812, compound

HRID 1031935Notes

Reaction equation

HRID 1031935 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[CH2:12]([N:16]1[C:25](=[O:26])[CH2:24][C:19]2([CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:18][C:17]1=[O:27])[CH2:13][CH:14]=[CH2:15]>C(Cl)Cl>[O:9]1[CH2:15][CH:14]1[CH2:13][CH2:12][N:16]1[C:17](=[O:27])[CH2:18][C:19]2([CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:24][C:25]1=[O:26]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 15169813HCID 15169813, compound

Product 1

HCID 15169812HCID 15169812, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of MCPBA (80%, 5.01 g, 1.13 equiv) in 50 mL of CH2Cl2 was added to a stirring solution of 8-(3-butenyl) -8-azaspiro[4.5]decane-7,9-dione (4.54 g, 1.00 equiv) in 0 mL of CH2Cl2. The resulting solution was stirred until TLC inspection indicated the absence of limiting reagent (δ15 h). The reaction was quenched with 40 mL of 2% Na2CO3 solution and transferred to a separatory funnel. The layers were separated and the organic phase was washed with 2% Na solution (3×20 mL). The combined aqueous layers were back-extracted with CH2Cl2 (40 mL). The combined organic layers were dried on anhydrous Na2SO4, filtered and the solvent removed in vacuo. Flash chromatography of the resulting residue in 25% EtOAc/hexane afforded the title compound (3.65 g, 75%) as a clear, viscous liquid.

Workup

  1. customThe reaction was quenched with 40 mL of 2% Na2CO3 solution
  2. customtransferred to a separatory funnel
  3. customThe layers were separated
  4. washthe organic phase was washed with 2% Na solution (3×20 mL)
  5. extractionThe combined aqueous layers were back-extracted with CH2Cl2 (40 mL)
  6. dry with materialThe combined organic layers were dried on anhydrous Na2SO4
  7. filtrationfiltered
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-fbf9609680d14053bf1ce0d77e37b4a1
Source dataset
uspto-grants-1990_09
Patent number
US04956368

Reaction notes

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