Methyl p-toluenesulfonate → N-[1-(S)-[alpha-(R)-methoxybenzyl)-3-methyl-butyl]phthalimide

HRID 1935422Notes

Reaction equation

HRID 1935422 reaction equation
[OH:1][C@@H:2]([C@@H:9]([N:14]1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24])[CH2:10][CH:11]([CH3:13])[CH3:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:25]1(C)C=CC(S(OC)(=O)=O)=CC=1.[H-].[Na+]>C1(C)C=CC=CC=1>[CH3:25][O:1][C@@H:2]([C@@H:9]([N:14]1[C:15](=[O:24])[C:16]2=[CH:23][CH:22]=[CH:21][CH:20]=[C:17]2[C:18]1=[O:19])[CH2:10][CH:11]([CH3:13])[CH3:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6645Methyl p-toluenesulfonateHCID 24758Sodium hydrideHCID 12087153N-[1-(S)-[alpha-(R)-hydroxybenzyl]-3-methylbutyl]phthalimide

Product 1

HCID 18741230N-[1-(S)-[alpha-(R)-methoxybenzyl)-3-methyl-butyl]phthalimide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of N-[1-(S)-[α-(R)-hydroxybenzyl]-3-methylbutyl]phthalimide (30.4 g, 94.0 mmol.) in toluene (380 mL) were successively added methyl p-toluenesulfonate (19.2 g, 103 mmol.) and 60% sodium hydride (4.13 g, 103 mmol.). The resulting mixture was heated under reflux for 18 hours under stirring, cooled to room temperature, successively washed with water and aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by middle pressure column chromatography (n-hexane/ethyl acetate=5/1), to give N-[1-(S)-[α-(R)-methoxybenzyl]-3-methylbutyl]phthalimide as a white crystalline product (25.6 g, yield: 81%).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 18 hours
  3. washsuccessively washed with water and aqueous saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was purified by middle pressure column chromatography (n-hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-db7dc8ea1cbe4d0b9401ea7af0ffc30e
Source dataset
uspto-grants-2002_05
Patent number
US06387908B1

Reaction notes

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