1-Chloroethyl chloroformate → HCID 9806285, compound

Participants

Reaction Steps

1'-Methyl-5-[4-(2-methyl-6-(2-oxopyrrolidin-1-yl)pyridin-3-yl]benzoyl]-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine] (E5, 0.30 g, 0.59 mmol) was stirred under argon in 1,2-dichloroethane (20 ml) with dilsopropylethylamine (0.15 ml, 0.89 mmol) and 1-chloroethyl chloroformate (0.16 ml, 1.5 mmol) for 16 h. The mixture was concentrated in vacuo, and the residue was heated at reflux in methanol (100 ml) for 1.5 h. The solution was evaporated to dryness, and this residue was dissolved in dichloromethane, washed with 10% Na2CO3, dried (Na2SO4) and evaporated to dryness. The material was purified by conversion to the N-t-butoxycarbonyl derivative (di-t-butyldicarbonate, CH2Cl2, 1h), chromatography, and deprotection with trifluoroacetic acid to afford the title compound. The hydrochloride salt was formed by dissolution in dichloromethane, treatment with 1 M HCl in Et2O, and trituration in acetone. This gave 0. 123 g, 39% of a white powder.

Provenance & Evidence