Trifluoroacetic acid → HCID 71293825, compound

Participants

Reaction Steps

A mixture of tert-butyl 4-[(3R*,4S*)-3-[(2-tert-butoxy)-2-oxoethyl]-1-[(2-chloro-6-methylphenyl)methyl]-4-methylpyrrolidin-3-amido}piperidine-1-carboxylate obtained in Example 8a (237 mg, 0.42 mmol), trifluoroacetic acid (2.3 ml, 31 mmol) and dichloromethane (dehydrated) (2.3 ml) was stirred at mom temperature for three hours and 30 minutes. The reaction mixture was concentrated, and cyclopent-1-ene-1-carbaldehyde obtained in Example 7a (121 mg, 1.26 mmol), triethylamine (0.176 ml, 1.26 mmol) and tetrahydrofuran (5 ml) were added to the resulting residue, followed by stirring for 35 minutes. Sodium triacetoxyborohydride (267 mg, 1.26 mmol) was added to the reaction mixture, which was stirred at room temperature for 13 hours. The reaction mixture was concentrated, and the resulting residue was purified by silica gel column chromatography (ODS silica gel, elution solvent: water/methanol) twice to give the title compound (88 mg, yield 42.9%).

Provenance & Evidence