Potassium Iodide → (R)-1-(2-hydroxyethyl)nipecotic acid ethyl ester

Participants

Reaction Steps

The (R)-enantiomer of ethyl nipecotate (100 g, 0.64 mole) (Akkerman, A. M. et al., Gazz.Chim.Ital., 102 (1972) 189) was mixed in dry acetone (300 ml) with 2-bromoethanol (85 g, 0.68 mole), dried, powdered potassium carbonate (188 g, 1.28 mole) and potassium iodide (21.6 g, 0.13 mole). The reaction mixture was stirred at room temperature for 18 h and at reflux for 24 h. Filtration of the reaction mixture and evaporation of the resultant filtrate gave (R)-1-(2-hydroxyethyl)nipecotic acid ethyl ester as an oil, which was purified by distillation in vacuo (110-115C, 0.1 mmHg), yield (72.2 g, 56%). TLC: rf=0.20 (SiO2; dichloromethane/methanol=19:1).

Provenance & Evidence