1-Chloroethyl chloroformate → 2-Methyl-5-(pyrrolidin-3-yloxy)-1h-indole-3-carboxylic acid benzyl ester, hydrochloride

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Reaction Steps

5-(1-benzyl-pyrrolidin-3-yloxy)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (0.118 g, 0.268 mmol, 1.0 eq.) was dissolved in dry 1,2-dichloroethane (5 mL) and treated with α-chloroethyl chloroformate (0.035 mL, 0.32 mmol, 1.2 eq.). The reaction was heated to reflux and followed by TLC (hexane/ethyl acetate 1/1). After 2 hours, the reaction was concentrated in vacuo, redissolved in methanol (5 mL), and heated to reflux. After 4 hours, the crude hydrochloride salt was precipitated from methanol/ethyl acetate/hexane to afford a brown solid, which was carried directly to the next step.

Provenance & Evidence