TBAF tetrahydrofuran → 4-{[(4-Hydroxy-2-methyl-phenyl)-methyl-amino]-methyl}-2-methyl-benzoic Acid Methyl Ester

HRID 2261814Notes

Reaction equation

HRID 2261814 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][Si](C(C)(C)C)(C)C)=[CH:15][C:14]=2[CH3:27])[CH3:12])=[CH:6][C:5]=1[CH3:28].CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>C1COCC1>[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:14]=2[CH3:27])[CH3:12])=[CH:6][C:5]=1[CH3:28]

Participants

4

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 667041694-({[4-(Tert-butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-methyl-amino}-methyl)-2-methyl-benzoic acid methyl ester

Product 1

HCID 574433374-{[(4-Hydroxy-2-methyl-phenyl)-methyl-amino]-methyl}-2-methyl-benzoic Acid Methyl EsterYield 71.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-({[4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-methyl-amino}-methyl)-2-methyl-benzoic acid methyl ester (1.0 g, 2.1 mmol) in THF (20.0 mL) is added 1.0 M TBAF/THF (3.2 mL, 3.2 mmol) at room temperature. The reaction mixture is stirred for 1.0 h. The mixture is partitioned between EtOAc (30 mL) and water (30 mL). The organic phase is washed with brine (30 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to a residue. The residue is purified by flash chromatography to afford the title compound as oil (0.45 g, 62%). LC-ES/MS m/e 300.3 (M+1), 298.3 (M−1).

Workup

  1. customThe mixture is partitioned between EtOAc (30 mL) and water (30 mL)
  2. washThe organic phase is washed with brine (30 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure to a residue
  6. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-13b92a529c3a49a89d5652b442598d62
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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