Propionic Acid → HCID 20196392, compound

Participants

Reaction Steps

148 ml of 1.67M boron hydride in tetrahydrofurane were added to a solution of 11.3 g of N-[2-(3-benzyloxy-4-hydroxyphenyl)-ethyl]-4-benzyloxy-mandelamide (obtained as described in example 67) in 100 ml of tetrahydrofurane. After 3 hours under reflux, the mixture was cooled and 6.93 g of propionic acid were added. The mixture was refluxed again for 1 hour and then evaporated to dryness. The resulting oil was dissolved in methylene chloride, washed with water and diluted sodium hydroxide, dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by chromatography on silica gel column using methylene chloride/methanol/ammonium hydroxide=97/3/0.3 as eluent. N-[2-(4-Benzyloxyphenyl)-2-hydroxyethyl]-3-O-benzyldopamine was thus obtained, m.p. 124°-125° C. (from ethanol).

Provenance & Evidence