Reaktion #48729

Reaktionsgleichung

isobutylchloroformate

N-methylmorpholine

(+/−)-trans-cyclopropane-1,2-dicarboxylic acid monoethyl ester

sodium borohydride

→

desired compound

Ausbeute 49.2%

(+/−)-trans-2-hydroxymethyl-cyclopropanecarboxylic acid ethyl ester

Ausbeute 49.2%

Lösungsmittel

water

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturWarm to room temperature over night
2. 2
   ExtraktionRemove tetrahydrofuran under reduced pressure and extract aqueous layer with diethyl ether (3×20 mL)
3. 3
   WaschenWash
4. 4
   Trocknendry over magnesium sulfate
5. 5
   EinengenConcentrate under reduced pressure
6. 6
   Wascheneluting with 25-65% ethyl acetate in hexanes

Vorschrift

Add isobutylchloroformate (0.41 mL, 3.16 mmol) and N-methylmorpholine (0.35 mL, 3.16 mmol) to a solution of (+/−)-trans-cyclopropane-1,2-dicarboxylic acid monoethyl ester (0.50 g, 3.161 mmol) in tetrahydrofuran (21 mL) at −50° C. Stir for 5 minutes and then filter into a slurry of sodium borohydride (0.084 g, 2.21 mmol) in tetrahydrofuran (9 mL) and cool to −50° C. Warm to room temperature over night and then add 9 mL of water. Remove tetrahydrofuran under reduced pressure and extract aqueous layer with diethyl ether (3×20 mL). Wash combined organic layers with saturated aqueous sodium chloride and dry over magnesium sulfate. Concentrate under reduced pressure and subject residue to silica gel chromatography eluting with 25-65% ethyl acetate in hexanes to provide the desired compound (0.224 g, 49.1%).

Quelle