Lithium Hydroxide → cis-1-Benzoyl-4-hydroxy-L-proline

Participants

Reaction Steps

A solution of lactone from Example 1, part A(5) (10.05 gm, 46.31 mmole) in THF-H2O (100 ml -18 ml) was treated slowly with 1M lithium hydroxide (60 ml). The reaction was stirred at room temperature under argon for 2 hours, concentrated and acidified to pH 6 with HCl. The solution was washed several times with ethyl acetate, acidified to pH 1 with HCl, saturated with sodium chloride and extracted with ethyl acetate. The extracts were washed with brine, dried over sodium sulfate, filtered and concentrated to an oil which was crystallized from dichloromethane-hexane to afford 7.7 gm (71%) of the title compound.

Provenance & Evidence