Lithium borohydride → HCID 58386143, compound

Participants

Reaction Steps

To a solution of 3-benzyl 4-ethyl 1-(4-chlorophenyl)-1H-pyrazole-3,4-dicarboxylate (Example 1C, 3.57 g, 9.28 mmol) in THF (100 mL) was added LiBH4 solution (7.89 mL, 15.77 mmol, 2M in THF). The reaction mixture was stirred at room temperature for 5 h. The resulting mixture was quenched with aqueous sat. NH4Cl solution (10 mL). Solvent was evaporated and the crude product was diluted with H2O (30 mL), extracted with EtOAc (150 mL). The organic layer was separated, dried over MgSO4 and concentrated to give a crude product which was further purified by ISCO automated chromatography (42 g, Hexane/EtOAc, 100:0 to 60:40 gradient) to give the product as a white solid (1.5 g, 58% yield). 1H NMR (CDCl3) δ 1.40 (t, J=7.2 Hz, 3H), 4.38 (q, J=7.2 Hz, 2H), 3.98 (t, J=7.1 Hz, 1H). 4.88 (d, 7.1 Hz, 2H), 7.40-7.48 (m, 2H), 7.60-7.67 (m, 2H), 8.32 (s, 1H). LC-MS, [M+H]+=281.0.

Provenance & Evidence