Oxalic Acid → (r)-2-[4-[2-(t-Butyloxycarbonylamino)propoxy]phenyl]-3-[4-[2-(1-pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophene oxalate

Participants

Reaction Steps

By essentially following the conditions described in Example 20, Part B, adding the diethyl azodicarboxylate to a mixture of triphenylphospine, 2-(4-hydroxyphenyl)-3-[4-[2-(1-pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophene (Part A) and (R)-(−)-N-t-Boc-2-amino-1-propanol (Part B) in THF at 0° C. and stirring the reaction mixture at ambient temperature about 16 h, the free base of the title compound was prepared as a foam in 65% yield following flash chromatography (SiO2; 1% then 3% then 5% MeOH in CHCl3 sat'd with NH4OH). The foam was taken up in a minimal amount of MeOH and treated with a solution of oxalic acid in MeOH to provide the oxalate salt.

Provenance & Evidence