Ethyl orthoformate → HCID 18426271, compound

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Reaction Steps

A solution of 4-{N-(2-amino-5-bromobenzoyl)glycyl}aminomethyl-1-(4-chlorobenzyl)piperidine (Compound No. 1042) (50 mg, 0.10 mmol) in triethyl orthoformate (6.5 mL) was stirred at 150° C. for 17 h. Concentration afforded a yellow solid. To a solution of the yellow solid in ethanol (3 mL) was added sodium borohydride (7.6 mg, 0.2 mmol) and the mixture was stirred at room temperature for 14 h. A resulting white precipitate was resolved in dichloromethane and the solution was washed with 1 N aqueous NaOH (2 mL). The organic layer was separated, dried over K2CO3, filtered and evaporated. Column chromatography (SiO2, 20% MeOH/CHCl3) gave 4-[N-{5-bromo-2-(methylamino)benzoyl)glycyl]aminomethyl-1-(4-chlorobenzyl)piperidine (Compound No. 1427) (40 mg, 80%) The purity was determined by RPLC/MS (100%); ESI/MS m/e 505 (C23H28BrClF6N4O2).

Provenance & Evidence