Sodium hydride → HCID 23081216, compound

HRID 856117Notes

Reaction equation

HRID 856117 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[O:9]=[C:10]([CH3:26])[CH2:11][N:12]1[CH2:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14][CH2:13]1>CS(C)=O>[CH3:26][C:10]1([CH2:11][N:12]2[CH2:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14][CH2:13]2)[CH2:2][O:9]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 23081584HCID 23081584, compound

Product 1

HCID 23081216HCID 23081216, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Trimethylsulfoxonium iodide (22.95 g, 104 mmol) was gradually added to a suspension of sodium hydride (4.3 g, 109 mmol) in DMSO (200 ml), and the mixture was stirred at room temperature for 2 hours. To which a solution tert-butyl 4-(2-oxopropyl)homopiperazine-1-carboxylate (24.3 g, 94.8 mmol) prepared in Reference Example 10 in DMSO (25 ml) was gradually added dropwise, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into ice water, and extracted with diethyl ether. The extract was washed with water, and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1) to afford tert-butyl 4-(2-methyl-2-oxiranylmethyl)homopiperazine-1-carboxylate (15.38 g, yield 60%) as a pale yellow oil.

Workup

  1. additionwas gradually added dropwise
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. extractionextracted with diethyl ether
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1)

Sources & evidence

ORD record
ord-23e2228d22534c14a4d5ef240c6b58b1
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

Loading…