Reaktion #78935

Reaktionsgleichung

MsCl

[1-(4-chloro-phenyl)-cyclopentyl]-(3-hydroxymethyl-piperidin-1-yl)-methanone

iPr2NEt

→

desired compound

Methanesulfonic acid 1-[1-(4-Chloro-phenyl)-cyclopentanecarbonyl]-piperidin-3-ylmethyl ester

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenbefore concentrating
2. 2
   Sonstigepurifying the resulting residue by silica gel chromatography (gradient 2.5-100% EtOAc in hexane)

Vorschrift

To a solution of [1-(4-chloro-phenyl)-cyclopentyl]-(3-hydroxymethyl-piperidin-1-yl)-methanone (0.5 g, 1.55 mmol) in dichloromethane (9.5 mL) at room temperature was added iPr2NEt (0.5 g, 3.9 mmol) followed by MsCl (0.214 g, 1.86 mmol). The reaction mixture was allowed to stir for one hour before concentrating and purifying the resulting residue by silica gel chromatography (gradient 2.5-100% EtOAc in hexane). The desired compound was obtained as an oil (0.345 g, 56%). 13C (100 MHz, CDCl3, partial) δ174.0, 144.0, 131.8, 128.8, 126.5, 70.8, 58.1, 35.3, 26.5, 24.9. 1H (300 MHz, CDCl3) δ7.26-7.24 (m, 2H), 7.13-7.10 (m, 2H), 4.61-1.86 (m, 19H), 1.67 (s, 3H).

Quelle