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

HRID 424809Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 424809
[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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 574433374-{[(4-Hydroxy-2-methyl-phenyl)-methyl-amino]-methyl}-2-methyl-benzoic Acid Methyl EsterAusbeute 71,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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 reaction 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 give the title compound as oil (0.45 g, 62%). LC-ES/MS: 300.3 (M+1), 298.3 (M−1).

Aufarbeitung

  1. customThe reaction 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

Quellen und Nachweise

ORD-Eintrag
ord-7ce31479ea2f4d0dbfcaf2ece218acd7
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106077B2

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