Methyl iodide → HCID 66971294, compound

HRID 1361320Notes

Reaction equation

HRID 1361320 reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][C@H:10]([N:13]([CH:21]2[CH2:26][CH2:25][C:24]([CH3:28])([CH3:27])[CH2:23][CH2:22]2)[C:14](=[O:20])[C:15]([CH3:19])([CH3:18])[CH2:16][OH:17])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[H-].[Na+].I[CH3:32]>C1COCC1>[C:1]([N:8]1[CH2:12][CH2:11][C@H:10]([N:13]([C:14](=[O:20])[C:15]([CH3:19])([CH3:18])[CH2:16][O:17][CH3:32])[CH:21]2[CH2:26][CH2:25][C:24]([CH3:28])([CH3:27])[CH2:23][CH2:22]2)[CH2:9]1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66971267HCID 66971267, compound

Product 1

HCID 66971294HCID 66971294, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3S)-1-Boc-3-[(4,4-dimethylcyclohexyl)(3-hydroxy-2,2-dimethylpropanoyl)amino]pyrrolidine (800 mg, 2.02 mmol) prepared in Step B of Example A8 in THF was added NaH (73 mg, 3.03 mmol) and iodomethane (430 mg, 3.03 mmol) at 0° C., and the solution was stirred at rt for 2 h. After the reaction finished, the solution was concentrated in vacuo, extracted with 1N-HCl and EtOAc. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by column chromatography (eluent: EtOAc/Hex=1/2) to give the title compound (784 mg, 94.6%).

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. extractionextracted with 1N-HCl and EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (eluent: EtOAc/Hex=1/2)

Sources & evidence

ORD record
ord-337ec102a7bc4b4197a8c0d62e4cccb0
Source dataset
uspto-grants-2011_02
Patent number
US07879852B2

Reaction notes

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