Diisopropylamine → HCID 18790037, compound

Participants

Reaction Conditions

Reaction Steps

Diisopropylamine (17.5 mL, 124 mmol) is dissolved in THF (80 mL), cooled to -40° C. and 2.38 M n-butyl lithium in hexanes (52 mL, 124 mmol) is added over 5 minutes. The reaction is allowed to warm to 0° C. and cyclopentanecarboxylic acid (6.7 mL, 62 mmol) in THF (60 mL) is added over 5 minutes. The reaction is heated at 40° C. for 1 hour. The reaction is cooled to -78° C. and 5-phenylpentanal (10 g, 62 mmol) in THF (20 mL) is added dropwise over 15 minutes. The cooling bath is removed and the reaction is allowed to stir at room temperature overnight. The reaction is acidified with 2 N HCl (120 mL) and the organics are removed in vacuo. The resulting aqueous mixture is extracted with CH2Cl2 (200 mL) and this organic layer is dried over MgSO4. The solution is concentrated in vacuo, and the resulting residue is purified by column chromatography (silica, 50% ether in petroleum ether) to yield 1-(1-hydroxy-5-phenylpentyl)cyclopentanecarboxylic acid (13.1 g, 77%): 1H NMR (300 MHz, CDCl3) δ 7.29-7.24 (m, 2H), 7.19-7.15 (m, 3H), 3.53-3.46 (m, 1H), 2.64-2.58 (m, 2H), 2.20-2.13 (m, 1H), 2.07-1.99 (m, 1H), 1.95-1.73 (m, 1H), 1.67-1.49 (m, 8H), 1.44-1.32 (m, 3H); MS (EI) m/e 276 (M+).

Provenance & Evidence