Water → HCID 21911988, compound

HRID 1245439Notes

Reaction equation

HRID 1245439 reaction equation
[N:1]([CH2:4][CH2:5][CH:6]([CH3:11])[C:7]([O:9][CH3:10])=[O:8])=[N+:2]=[N-:3].[CH:12]([N-]C(C)C)(C)C.[Li+].C1CCCCC1.IC.O>O1CCCC1>[N:1]([CH2:4][CH2:5][C:6]([CH3:12])([CH3:11])[C:7]([O:9][CH3:10])=[O:8])=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 13839120Methyl 4-azido-2-methylbutanoateHCID 86604122LDA cyclohexane

Product 1

HCID 21911988HCID 21911988, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.3 g of methyl 4-azido-2-methylbutyrate (which was prepared by the method as described in Tetrahedron, 1987, 43, 1811–1822) in 13 ml of tetrahydrofuran, 16.7 ml of 1.5N lithium diisopropylamide-cyclohexane solution was added at −78° C. in nitrogen atmosphere, followed by 30 minutes' stirring at the same temperature. To the solution 1.6 ml of iodomethane was added at −78° C., followed by 30 minutes' stirring at the same temperature. Water was added to the reaction liquid, followed by extraction with diethyl ether. The diethyl ether layer was washed with saturated brine, dried on anhydrous magnesium sulfate and the solvent was distilled off. The residue was separated and purified on silica gel column chromatography (ethyl acetate/hexane=1/30) to provide 406 mg of the title compound.

Workup

  1. waitfollowed by 30 minutes
  2. stirring' stirring at the same temperature
  3. extractionfollowed by extraction with diethyl ether
  4. washThe diethyl ether layer was washed with saturated brine
  5. dry with materialdried on anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customThe residue was separated
  8. custompurified on silica gel column chromatography (ethyl acetate/hexane=1/30)

Sources & evidence

ORD record
ord-c48c617f215c43fcabb27b9e83aea82e
Source dataset
uspto-grants-2006_10
Patent number
US07125877B2

Reaction notes

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