Aluminium lithium hydride → HCID 58724177, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 1-(4-(2-chlorophenylsulfonyl)piperazin-1-yl)cyclobutanecarboxylate (47 mg, 0.13 mmol) was dissolved in THF (3 ml). Lithium aluminum hydride (0.32 ml, 1.0 M in THF) was added at 0° C. The reaction mixture was stirred at 0° C. for 45 minutes. It was quenched by careful addition of EtOAc at 0° C. The mixture was stirred for another 30 minutes before 1N NaOH and equal volume of brine were added. The mixture was extracted with EtOAc three times. Combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography (SiO2, 70% EtOAc/hexanes) to give the title compound (20 mg, 8% 3 steps) as a colorless oil. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm: 0.51-0.54 (m, 2 H), 0.60-0.63 (m, 2 H), 1.74 (bs, 1 H), 2.80-2.84 (m, 4 H), 3.17-3.24 (m, 4 H), 3.56 (s, 2 H), 7.38 (td, J=7.4, 1.6 Hz, 1 H), 7.45-7.52 (m, 2 H), 8.00 (dd, J=7.7, 1.6 Hz, 1 H); 13C NMR (100 MHz, CHLOROFORM-D) δ ppm 12.2, 46.5, 46.6, 49.7, 64.7, 127.0, 132.1, 132.3, 132.4, 133.6, 135.9; ESI-MS: m/z 331.2 (M+H)+.

Provenance & Evidence