Reaktion #511989

Reaktionsgleichung

[4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-methyl-amine

4-formyl-2-methyl-benzoic acid methyl ester

acetic acid

sodium triacetoxyborohydride

→

title compound

Ausbeute 115.1%

{[4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-methyl-amino}-methyl-2-methyl-benzoic acid methyl ester

Ausbeute 115.1%

Lösungsmittel

1,2-dichloroethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction is quenched with 5% aq. sodium bicarbonate (5 mL)
2. 2
   Sonstigeis partitioned between EtOAc (60 mL) and water (50 mL)
3. 3
   WaschenThe organic layer is washed with brine (50 mL)
4. 4
   Trocknendried (Na2SO4)
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe residue is purified by flash column chromatography

Vorschrift

To a solution of [4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-methyl-amine (0.64 g, 2.6 mmol) and 4-formyl-2-methyl-benzoic acid methyl ester (0.38 g, 2.1 mmol), acetic acid (0.25 g, 4.2 mmol) in 1,2-dichloroethane (10.0 mL) is added sodium triacetoxyborohydride (0.89 g, 4.2 mmol) in portions. The mixture is stirred at room temperature overnight. The reaction is quenched with 5% aq. sodium bicarbonate (5 mL) and is partitioned between EtOAc (60 mL) and water (50 mL). The organic layer is washed with brine (50 mL), dried (Na2SO4), filtered, and concentrated. The residue is purified by flash column chromatography to afford the title compound as a syrup (1.0 g, 95%). LC-ES/MS m/e 414.3 (M+1).

Quelle