Water → HCID 86604797, compound

HRID 856120Notes

Reaction equation

HRID 856120 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[CH3:9][N:10]([CH:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25](=[O:27])[CH3:26])[CH2:20][CH2:19]1)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14].O>CS(C)=O>[CH3:9][N:10]([CH:18]1[CH2:19][CH2:20][N:21]([CH2:24][C:25]2([CH3:2])[CH2:26][O:27]2)[CH2:22][CH2:23]1)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:14])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 69479336HCID 69479336, compound

Product 1

HCID 86604797HCID 86604797, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Trimethylsulfoxonium iodide (1.96 g, 8.89 mmol) was gradually added to a suspension of sodium hydride (372 mg, 9.32 mmol) in dimethylsulfoxide (20 ml), and the mixture was stirred at room temperature for 1.5 hours. To which a solution of tert-butyl N-methyl-[1-(2-oxopropyl)piperidin-4-yl]carbamate (2.3 g, 8.5 mmol) in dimethylsulfoxide (20 ml) was added, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into iced water, and extracted with diethyl ether. The extract was washed with a saturated saline solution, dried over magnesium sulfate, and then filtered. The resultant filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1) to afford tert-butyl N-methyl-[1-(2-methyl-2-oxiranylmethyl)piperidin-4-yl]carbamate (2.1 g, yield 86%) as a light yellow oily material.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. extractionextracted with diethyl ether
  3. washThe extract was washed with a saturated saline solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe resultant filtrate was concentrated under a reduced pressure
  7. customthe residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1)

Sources & evidence

ORD record
ord-11e279fd709740a18a02ef871395565f
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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