Reaktion #46142

Reaktionsgleichung

nipecotic acid

sodium hydroxide

benzylchloroformate

sodium hydroxide

→

titled compound

(±)-1-[(Benzyloxy)carbonyl]piperidine-3-carboxylic acid

Lösungsmittel

water

tetrahydrofuran

water

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter 24 hours tetrahydrofuran was removed in vacuo
2. 2
   Extraktionextracted with dichloromethane (3×)
3. 3
   TrocknenThe combined organic portions were dried with anhydrous magnesium sulfate
4. 4
   FiltrationFiltration
5. 5
   Sonstigefollowed by evaporation of the filtrate in vacuo

Vorschrift

To an ice cooled solution of nipecotic acid (10.0 g, 77.5 mmol), sodium hydroxide (3.4 g, 85 mmol), and tetrahydrofuran (50 mL) in water (100 mL) was added by simultaneous dropwise addition benzylchloroformate (13.3 mL, 93 mmol) in tetrahydrofuran (50 mL) and sodium hydroxide (3.4 g, 85 mmol) in water (50 mL). Warmed slowly to room temperature. After 24 hours tetrahydrofuran was removed in vacuo and the resulting aqueous mixture acidified with 3 N hydrochloric acid and extracted with dichloromethane (3×). The combined organic portions were dried with anhydrous magnesium sulfate. Filtration followed by evaporation of the filtrate in vacuo gave the titled compound. 1HNMR (CHCl3, 300 MHz) □ 7.45-7.20 (m, 5H); 5.14 (m, 2H); 4.21 (br s, 1H); 3.96 (m, 1H), 3.15 (br s, 1H); 2.93 (m, 1H); 2.51 (m, 1H); 2.09 (m, 1H); 1.80-1.60 (m, 2H); 1.50 (m, 1H) ppm.

Quelle