Lithium hydroxide, monohydrate → HCID 23627747, compound

Participants

Reaction Steps

A solution of [(S)-2-Benzyl-4-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazin-1-yl]-acetic acid methyl ester (Example 57) (342 mg, 0.78 mmol) in THF (5 mL) at room temperature was treated with an aqueous solution (1 mL) containing lithium hydroxide monohydrate (36 mg, 0.858 mmol). The reaction mixture was allowed to stir for 2 h and then evaporated to a small volume. The reaction mixture was then dissolved in water (5 mL) and the pH adjusted to ˜7 with 1 N HCl to precipitate product. The precipitate was then triturated with water (2×5 mL) and dried under a stream of nitrogen to afford product as a colorless solid (318 mg, 96%). 1H NMR (CDCl3) 1.43-1.57 (m, 2H), 1.77-1.79 (m, 6H), 3.02-3.15 (m, 2H), 3.27 (br s, 2H), 3.51 (br s, 1H), 3.74 (s, 3H), 3.77-3.89 (m, 2H), 4.57-4.59 (m, 1H), 6.24-6.31 (m, 2H), 6.55 (br s, OH), 6.67 (d, J=8.6, 1H) 7.18-7.27 (m, 5H). LC/MS 5.34 min, [M+1]+ 425.

Provenance & Evidence