Lithium hydroxide, monohydrate → 3-(5-(Tert-butoxy)-5-oxopentyl)-2-(4-fluorophenyl)-1-oxo-1,2-dihydroisoquinoline-6-carboxylic acid

Participants

Reaction Steps

LiOH.H2O (0.229 g, 5.47 mmol) was added to a stirred, room temperature mixture of methyl 3-(5-(tert-butoxy)-5-oxopentyl)-2-(4-fluorophenyl)-1-oxo-1,2-dihydroisoquinoline-6-carboxylate (1.24 g, 2.73 mmol) in MeOH (5 mL), tetrahydrofuran (5.00 mL) and water (5.00 mL) and the mixture was stirred at room temperature for 3 h. The reaction mixture was diluted with diethyl ether (10 mL), water (5 mL) was added, the aqueous layer was separated, acidified with hydrochloric acid (2 M) to pH 2-3, extracted with dichloromethane (2×30 mL), the combined organic was dried (MgSO4), filtered and concentrated to give 3-(5-(tert-butoxy)-5-oxopentyl)-2-(4-fluorophenyl)-1-oxo-1,2-dihydroisoquinoline-6-carboxylic acid (1.153 g, 2.62 mmol) as a yellow solid.

Provenance & Evidence