Hydrogen Bromide → 3-(4-Hydroxyphenyl)proline, ethyl ester hydrobromide

Participants

Reaction Steps

A solution of N-acetyl-2-ethoxycarbonyl-3-(4-methoxyphenyl)proline ethyl ester (10 g, 27 mmol) in aqueous HBr (48%, 40 mL) and HOAc (10 mL) was heated at 120° C. under a nitrogen atmosphere overnight. The reaction mixture was concentrated in vacuo, and the residue was azeotroped with acetonitrile (2×) and Et2O/toluene (1×) to yield 3-(4-hydroxyphenyl)proline, ethyl ester hydrobromide as a mixture of diastereomers.

Provenance & Evidence