Ethyl Acetate → (1S,2R)-2-amino-1,2,3,4-tetrahydronaphthalen-1-ol

Participants

Reaction Steps

One gram of the hydroxamic acid of (1S,2R)-2-carboxy-1-hydroxytetralin is reacted with equimolar amounts of diethyl azodicarboxylate and triphenylphosphine in tetrahydrofuran at room temperature using the procedure of Bittner, Grinberg and Kartoon (Tet. Lett. 23, 1965-8 (1974)). The product is isolated by acidification and extraction of the reaction mixture with ethyl acetate, followed by basification of the resulting aqueous solution with NaOH, extraction with methyl t-butyl ether, drying of the extracts over MgSO4, filtration, and the removal of solvent by rotary evaporation. The product (1S,2R)-1-hydroxy-2-aminotetralin is isolated as a light yellow oil.

Provenance & Evidence