Lithium hydroxide, monohydrate → HCID 59735066, compound

Participants

Reaction Steps

A solution of methyl (1S,3R)-1-isopropyl-3-[methyl(tetrahydro-2H-pyran-4-yl)amino]cyclopentanecarboxylate (1.0 g, 3.5 mmol) in 1:1 THF/MeOH (20 mL) was treated with a solution of LiOH.H2O (735 mg) in 10 mL of water. After several hours very little hydrolysis was observed by HPLC-MS analysis so the reaction mixture was warmed to reflux and stirred for 2 days. The pH of the reaction mixture was then adjusted to 7 and the mixture was concentrated. The residue was suspended in 50% methanol/DCM, filtered, and the filtrate was concentrated to afford 900 mg of (1S,3R)-1-isopropyl-3-[methyl(tetrahydro-2H-pyran-4-yl)amino]cyclopentanecarboxylic acid which required no further purification.

Provenance & Evidence