Tetrabutylammonium Fluoride → N-{(1RS,2SR)-2-(3,4-dichlorobenzyl)-3-hydroxy-1-methylpropyl}phthalimide

HRID 1956068Notes

Reaction equation

HRID 1956068 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[Cl:32])[CH2:5][CH:6]([CH2:20][O:21][Si](C(C)(C)C)(C)C)[CH:7]([N:9]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]2[C:10]1=[O:19])[CH3:8].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[Cl:32])[CH2:5][CH:6]([CH2:20][OH:21])[CH:7]([N:9]1[C:10](=[O:19])[C:11]2=[CH:18][CH:17]=[CH:16][CH:15]=[C:12]2[C:13]1=[O:14])[CH3:8]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 19073670N-{(1RS,2SR)-2-(3,4-dichlorobenzyl)-3-(tert-butyldimethylsilyloxy)-1-methylpropyl}phthalimide

Product 1

HCID 19073790N-{(1RS,2SR)-2-(3,4-dichlorobenzyl)-3-hydroxy-1-methylpropyl}phthalimideYield 47.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.07 g of the phthalimide compound thus obtained was dissolved in 15 ml of tetrahydrofuran, and 2.6 ml of a 1M tetrahydrofuran solution of tetrabutylammonium fluoride was added thereto. The mixture was stirred at room temperature overnight. The reaction solution was evaporated to dryness under reduced pressure. Then, the residue was dissolved in a liquid mixture of water and ethyl ether. The organic layer was collected by separation and then dried over anhydrous magnesium sulfate. The drying agent was separated by filtration, and then the solvent was distilled off under reduced pressure. The residue was subjected to medium pressure liquid chromatography (hexane/ethyl acetate=4/1→2/1) to obtain 0.39 g (yield: 47%) of N-{(1RS,2SR)-2-(3,4-dichlorobenzyl)-3-hydroxy-1-methylpropyl}phthalimide.

Workup

  1. customThe reaction solution was evaporated to dryness under reduced pressure
  2. dissolutionThen, the residue was dissolved in a liquid mixture of water and ethyl ether
  3. customThe organic layer was collected by separation
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe drying agent was separated by filtration
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-b4266b8b6efb4026947f094855de484a
Source dataset
uspto-grants-1998_07
Patent number
US05777150

Reaction notes

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