Lithium Hydroxide → HCID 59180066, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 4-(3-cyanobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.065 g, 0.23 mmol) was dissolved in THF (1 mL) and MeOH (1 mL). Then LiOH (0.097 g, 2.31 mmol) in H2O (1 mL) was added and the reaction stirred at 40° C. for 16 h. The solvent was removed under reduced pressure, and the residue re-dissolved in about 5 mL H2O and acidified to pH 2-3 with 1 N HCl. The product was filtered off, and then dissolved in DMSO (about 15 mg/mL) and purified by reverse phase HPLC, eluting with a gradient of 40-80% MeOH: water (with 0.1% formic acid) to afford both 4-(3-carbamoylbenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid (77) and 4-(3-cyanobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid (75).

Provenance & Evidence