Sodium hydride → HCID 23081557, compound

HRID 856116Notes

Reaction equation

HRID 856116 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[O:9]=[C:10]([CH3:28])[CH2:11][N:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:14][CH2:13]1>CS(C)=O>[CH3:28][C:10]1([CH2:11][N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])[CH2:14][CH2:13]2)[CH2:2][O:9]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 11558165HCID 11558165, compound

Product 1

HCID 23081557HCID 23081557, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Trimethylsulfoxonium iodide (1.96 g, 8.91 mmol) was added to a suspension of sodium hydride (0.37 g, 9.32 mmol) in DMSO (20 ml) while cooling in an ice-bath, and the mixture was stirred at room temperature for 30 minutes. To the mixture a solution of benzyl 4-(2-oxopropyl)piperazine-1-carboxylate (2.24 g, 8.10 mmol) in DMSO (10 ml) was added, 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, dried over magnesium sulfate, and then concentrated under reduced pressure to afford benzyl 4-(2-methyl-2-oxiranylmethyl)piperazine-1-carboxylate (1.51 g, yield 64%) as a pale yellow oil.

Workup

  1. temperaturewhile cooling in an ice-bath
  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. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2d4f9c1809024948a0c61c61459fd78c
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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