Reaktion #82194

Reaktionsgleichung

α-isocyanato-valine methyl ester

pyridine-2-methanol

→

desired compound

Ausbeute 54.1%

N-((2-Pyridinyl)methoxycarbonyl)valine Methyl Ester

Ausbeute 54.1%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux under N2 atmosphere for 4 h
2. 2
   SonstigeThe solvent was removed in vacuo
3. 3
   Sonstigethe residue was purified by silica gel chromatography

Vorschrift

A solution of 0.78 g (5.0 mmol) of α-isocyanato-valine methyl ester and 0.55 ml (5.7 mmol) of pyridine-2-methanol in 30 mL of toluene was heated at reflux under N2 atmosphere for 4 h. The solvent was removed in vacuo, and the residue was purified by silica gel chromatography using 2% methanol in chloroform to give 0.72 g (54%) of the desired compound as an oil. 1H NMR (CDCl3) δ 0.91 (d, J=7 Hz, 3 H), 0.98 (d, J=7 Hz, 3 H), 2.19 (m, 1 H), 3.75 (s, 3 H), 4.32 (dd, J=9, 5 Hz, 1 H), 5.24 (s, 2 H), 5.39 (br d, 1 H), 7.23 (ddd, J=8, 4, 1 Hz, 1 H), 7.37 (d, J=8 Hz, 1 H), 7.70 (td, J=8, 2 Hz, 1 H), 8.60 (br d, 1 H). Mass spectrum: (M+H)+ =267.

Quelle