Toluene → N-[1-(S)-[alpha-(R)-methoxybenzyl)-3-methyl-butyl]phthalimide
Reaction equation
O[C@@H:2]([C@@:9](C)([N:13]1[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]2[C:14]1=[O:23])CCC)[C:3]1[CH:8]=CC=C[CH:4]=1.C1(C)C=CC(S([O:34][CH3:35])(=O)=O)=CC=1.[H-].[Na+].[C:39]1([CH3:45])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>>[CH3:35][O:34][C@@H:45]([C@@H:9]([N:13]1[C:14](=[O:23])[C:15]2=[CH:22][CH:21]=[CH:20][CH:19]=[C:16]2[C:17]1=[O:18])[CH2:2][CH:3]([CH3:4])[CH3:8])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1Participants
5
Procedure
To a solution of N-[1-(S)-[α-(R)-hydroxybenzyl-]-methylbutyl]phthalimide]30.4 g, 94.0 mmol.) in toluene (380 mL) were successively added methyl p-toluene-sulfonate (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-methyl-butyl]phthalimide as a white crystalline product (25.6 g, yield: 81%)
Workup
- temperatureThe resulting mixture was heated
- temperatureunder reflux for 18 hours
- washsuccessively washed with water and aqueous saturated sodium chloride solution
- dry with materialdried over anhydrous sodium sulfate
- distillationThe solvent was distilled off under reduced pressure
- customThe residue was purified by middle pressure column chromatography (n-hexane/ethyl acetate=5/1)
Sources & evidence
- ORD record
- ord-0dd3c17570f84eb6a2ede9bc4fa40b43
- Source dataset
- uspto-grants-2004_02
- Patent number
- US06689785B2
Reaction notes
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