2-Methyl-2-butene → HCID 71147218, compound

HRID 712797Notes

Reaction equation

HRID 712797 reaction equation
[CH:1]([CH:3]1[CH2:9][CH:8]2[CH:6]([CH2:7]2)[CH2:5][N:4]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:2].CC(=CC)C.[O-:22]Cl=O.[Na+]>CC(C)=O.O>[C:13]([O:12][C:10]([N:4]1[CH:3]([C:1]([OH:22])=[O:2])[CH2:9][CH:8]2[CH:6]([CH2:7]2)[CH2:5]1)=[O:11])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 91277295HCID 91277295, compound

Product 1

HCID 71147218HCID 71147218, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

To a mixture of tert-butyl 4-formyl-3-azabicyclo[4.1.0]heptane-3-carboxylate (D16) (615 mg, 2.73 mmol) in acetone/water (30/20 ml) NaH2PO4.2H2O (426 mg, 2.73 mmol), 2-methyl-2-butene (1.3 ml, 12.28 mmol) and NaClO2 (864 mg, 9.55 mmol) were added and the reaction mixture was stirred at RT overnight. Solvents were evaporated in vacuo and the remaining residue was taken up into EtOAc (10 ml) and water (10 ml). Phases were separated and the aqueous layer was extracted with EtOAc (2×10 ml). The combined organic extracts after solvent evaporation afforded the title compound (D17) (0.5 g).

Workup

  1. additionwere added
  2. customSolvents were evaporated in vacuo
  3. customPhases were separated
  4. extractionthe aqueous layer was extracted with EtOAc (2×10 ml)
  5. customThe combined organic extracts after solvent evaporation

Sources & evidence

ORD record
ord-2e21ac3ef9ba45af83a142df31530ef0
Source dataset
uspto-grants-2015_11
Patent number
US09181279B2

Reaction notes

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