Cyclopentanecarbaldehyde → (2-{[(3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-cyclopentyl-methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of (3,5-bis-trifluoromethyl-benzyl)-(2-bromo-5-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amine (117.4 mg, 0.21 mmol) in THF (0.5 mL) at 0° C. was added iPrMgCl/LiCl in THF (0.35 mL, 0.7 mmol). The mixture was stirred at 0° C. for 3 hours. Cyclopentanecarboxaldehyde (41 mg, 0.42 mmol) was added. The mixture was stirred at 0° C. for 3 hours, quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate. Combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by chromatography over 25+S Biotage silica column (eluted with 0-30% ethyl acetate in hexanes) to afford the title compound as a colorless oil (55.5 mg, 46%). 1H NMR (400 MHz, CDCl3) δ ppm 0.97-1.10 (m, 1H) 1.33-1.42 (m, 1H) 1.43-1.70 (m, 5H) 1.76-1.86 (m, 1H) 2.17-2.32 (m, 1H) 2.56 (s, 1H) 4.17-4.20 (m, 3H) 4.69-4.79 (m, 3H) 4.81 (s, 1H) 4.90 (d, J=15.77 Hz, 1H) 7.34 (s, 1H) 7.52 (d, J=8.71 Hz, 1H) 7.58 (d, J=8.30 Hz, 1H) 7.66 (s, 2H) 7.77 (s, 1H). MS (ES+) Calc: 581.2, Found: 582.4 (M+1).

Provenance & Evidence