N-Methylbenzylamine → HCID 12364327, compound

HRID 492913Notes

Reaction equation

HRID 492913 reaction equation
[H-].[Na+].[CH3:3][NH:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CC1C=CC(S(OC[C@@H:24]2[O:26][CH2:25]2)(=O)=O)=CC=1.O1CCC[CH2:28]1>>[CH2:5]([N:4]([CH3:28])[CH2:3][C@H:25]1[CH2:24][O:26]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 4

HCID 7669N-MethylbenzylamineHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 154187Glycidyl tosylate, (R)-

Product 1

HCID 12364327HCID 12364327, compoundYield 64%

Procedure

Sodium hydride (60%, 88 mg) was suspended in tetrahydrofuran (5 ml) at room temperature under nitrogen atmosphere, and N-methylbenzylamine (0.284 ml) was added dropwise while stirring. After 1 hour, (2R)-glycidyl tosylate (457 mg) was added thereto and the reaction mixture was stirred overnight at room temperature, then at 50° C. for 7.5 hours. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated to give a residue, which was the purified by silica gel column chromatography (eluent; ethyl acetate) to provide the titled compound (225 mg, 64%) as a colorless oil.

Workup

  1. stirringthe reaction mixture was stirred overnight at room temperature
  2. waitat 50° C. for 7.5 hours
  3. customThe reaction mixture was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated
  7. customto give a residue, which
  8. custompurified by silica gel column chromatography (eluent; ethyl acetate)

Sources & evidence

ORD record
ord-775796670e17412191fa2de65bfb7408
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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