Aluminium lithium hydride → (1-Benzyl-7-methylazepan-3-yl)methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 1-benzyl-7-methyl-2-oxoazepane-3-carboxylate (2-4, 3.8 g, 14 mmol, 1.0 equiv) in THF (70 mL) at 0° C. under nitrogen was added solid lithium aluminum hydride (2.6 g, 69 mmol, 5.0 equiv) and the resulting mixture was stirred at 0° C. for 1.5 hours. Excess LAH was quenched with water (2 mL) and 15% aqueous sodium hydroxide solution (2 mL). The mixture was dried over sodium sulfate and concentrated. The residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes gradient) to yield (1-benzyl-7-methylazepan-3-yl)methanol (2-5) as a clear oil. 1H NMR (400 MHz, CDCl3) 7.36 (m, 5H), 3.68-1.49 (m, 18H). LRMS m/z (M+H) 234.3 found, 234.2 required.

Provenance & Evidence