Triethylamine → HCID 14181424, compound

Participants

Reaction Steps

L-Proline t-butyl ester (6.9 g 0.04 mole) and triethylamine (14 ml, 0.1 mole) are dissolved in 200 ml of dichloromethane and stirred in an ice bath while 2-chloroethanesulfonyl chloride (8.2 g, 0.05 mole) in 100 ml of dichloromethane is added over 20 minutes. After stirring 2 hours, the mixture is washed with 5% potassium bisulfate solution, saturated sodium bicarbonate solution and brine, then evaporated in vacuo. The semi-solid residue is chromatographed on 350 ml. silica gel using 1:1 ethyl acetate/hexane as eluant. The main fraction, comprising N-(vinylsulfonyl)-L-proline t-butyl ester is crystallized from ether/hexane, m.p. 84°-87° (7.1 g, 68%).

Provenance & Evidence