Methyl iodide → HCID 58376043, compound

HRID 1942484Notes

Reaction equation

HRID 1942484 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH:28]([CH3:30])[CH3:29])[C@H:12]1[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@@H:15]([CH2:25][CH2:26][OH:27])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:31]I.[H-].[Na+].[Cl-].[NH4+]>O1CCCC1>[CH2:1]([O:8][C:9]([N:11]([CH:28]([CH3:30])[CH3:29])[C@H:12]1[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[C@@H:15]([CH2:25][CH2:26][O:27][CH3:31])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 58375893HCID 58375893, compound

Product 1

HCID 58376043HCID 58376043, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (2R,5R)-5-[[(benzyloxy)carbonyl](isopropyl)amino]-2-(hydroxy-ethyl)piperidine-1-carboxylate (2.10 g) in tetrahydrofuran (10 mL) was added methyl iodide (1.42 g), and the mixture was stirred. To the mixture was added 55% sodium hydride (300 mg) under ice-cooling, and the mixture was stirred at room temperature for 19 hours. To the reaction solution was added a saturated aqueous ammonium chloride solution (5 ml), and the mixture was extracted with ethyl acetate (50 ml). The organic layer was washed with water and a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (the developing solvent: hexane/ethyl acetate=4/1) to give the title compound (2.15 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 19 hours
  3. extractionthe mixture was extracted with ethyl acetate (50 ml)
  4. washThe organic layer was washed with water
  5. dry with materiala saturated aqueous sodium chloride solution, dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (the developing solvent

Sources & evidence

ORD record
ord-7bd4a35cfbb140388f171f4437f2ef06
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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