Lithium Hydroxide → HCID 59708800, compound

Participants

Reaction Steps

Aqueous lithium hydroxide (5 mL of a 4 M solution) was added to a solution of 11 (2.50 g, 6.50 mmol) stirring in tetrahydrofuran (40 mL). The reaction mixture was stirred at ambient temperature for 4 hours. The solvent was removed under vacuum and the residue dissolved in water (25 mL) and extracted with dichloromethane (1×25 mL). The aqueous solution was acidified to pH 6 as indicated by pH paper and extracted with ethyl acetate (3×25 mL). The acidic aqueous solution was evaporated to dryness and dried under vacuum to give the carboxylic acid 12 (3.58 g, quantitative yield) as a yellow foam: 1H NMR (300 MHz, CD3OD) δ 1.61-1.89 (m, 6H), 2.27-2.38 (m, 2H), 2.75-3.09 (m, 10H), 3.33-3.35 (m, 6H), 3.41 (t, J=6.3 Hz, 2H), 7.38-7.47 (m, 3H), 7.62-7.65 (m, 1H); ESI MS m/z 392 [C20H29N3O5+H]+.

Provenance & Evidence