Sodium Hydroxide → HCID 178482718, compound

Participants

Reaction Steps

A solution of intermediate 2, N-benzyl-N-methyl-3-oxocyclobutanecarboxamide (27.9 g, 0.128 mol) in absolute THF (40 mL) was added to a suspension of LiAlH4 (9.75 g, 0.257 mol) in absolute THF (200 ml) under stirring in argon. The mixture was refluxed under stirring for 1 h and cooled. Then 10 N NaOH (25 mL) and water (25 mL) were added. The organic layer was decanted, and the aqueous one was extracted with THF (2×50 mL). The organic layers were evaporated. The residue was purified by chromatography (silica gel, 63-100 μm, 300 g, CHCl3/MeOH 100:0→90:10). The title compound (25 g, 95%) was obtained as a colorless oil. 1H NMR-data (DMSO-d6): 7.19-7.33 (m, 5H, Ph); 4.85 (d, 1H, OH, J=6.6 Hz); 3.83-3.94 (m, 1H); 3.40 (s, 2H, CH2); 2.24-2.34 (m, 4H); 2.07 (s, 3H, NCH3); 1.81-1.92 (m, 1H); 1.34-1.44 (m, 2H).

Provenance & Evidence