Reaktion #477487

Reaktionsgleichung

[1,1′]binaphthalen-2-yl-di-tert-butyl-phosphane

6-bromo-2-methoxy-3-nitropyridine

Cs2CO3

(S)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

→

product

Ausbeute 7.5%

(S)-2-(6-Methoxy-5-nitro-pyridin-2-yloxymethyl)-pyrrolidine-1-carboxylic Acid Tert-Butyl Ester

Ausbeute 7.5%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter evaporation of the solvent under reduced pressure
2. 2
   Sonstigethe residue was purified by silica gel chromatography with dichloromethane/ethyl acetate/methanol (10:0:0; 9:0.5:0.5; 7:1.5:1.5; 0:5:5) as eluent

Vorschrift

To a mixture of Pd(OAc)2 (0.08 g, 0.34 mmol) and [1,1′]binaphthalen-2-yl-di-tert-butyl-phosphane (0.14 g, 0.34 mmol) in toluene (10 ml) was added 6-bromo-2-methoxy-3-nitropyridine(1.0 g, 4.29 mmol), Cs2CO3 (3.5 g, 10.73 mmol), and (S)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (1.73 g, 8.58 mmol). The mixture was stirred under nitrogen at room temperature for 24 h. After evaporation of the solvent under reduced pressure, the residue was purified by silica gel chromatography with dichloromethane/ethyl acetate/methanol (10:0:0; 9:0.5:0.5; 7:1.5:1.5; 0:5:5) as eluent to provide 0.11 g (7.5%) of the product.

Quelle