Triphenylphosphine → methyl 3-[(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-(2-chlorophenyl)ethoxy]-5-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1H-imidazo[4,5-c]pyridin-1-yl]thiophene-2-carboxylate

Participants

Reaction Steps

In a similar manner as described for example B31, 0.5 g of methyl 5-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1H-imidazo[4,5-c]pyridin-1-yl]-3-hydroxythiophene-2-carboxylate, 0.44 g of (1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-(2-chlorophenyl)ethanol (synthesized starting from (S)-(+)-2-chloromandelic acid in a two step sequence including reduction with LiAlH4 and protection of the primary hydroxy group using tert-butyldimethylsilylchloride), 0.63 g of triphenylphosphine (polymer bound, ˜3 mmol/g) and 0.55 g of di-tert-butyl azodicarboxylate in 10 ml anhydrous dichloromethane yield the title compound.

Provenance & Evidence