Diethyl Ether → HCID 15814288, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (+)-diisopinocamphenylchloroborane (3.8 g, 11.8 mmol) was dissolved in anhydrous THF (10 mL) under nitrogen and cooled to -35° C.; the product from Step A (0.8 g, 2.36 mmol) was added and this mixture was stirred at -35° C. for 24 hr. The solvent was evaporated and the residue was mixed with diethyl ether (15 mL) and diethanol amine (0.62 g, 5.9 mmol) was added followed by stirring for 2 h, filtration, and evaporation. The residue was purified by column chromatography (silica, hexane then hexane/ethyl acetate gradient) to give a colorless solid (0.60 g, 75%): mp 57°-58° C. The optical purity was established to be >90% ee by HPLC analysis of the diastereomeric esters formed with (S)-α-methoxyphenylacetic acid.

Provenance & Evidence