Methanol → HCID 68312803, compound

Participants

Reaction Steps

To an ice-cooled suspension of 1-benzylazepane-4-carbaldehyde hydrochloride (1.0 g, 3.95 mmol) in THF (15 mL) was added methylmagnesium bromide (3M in diethyl ether, 4 mL) dropwise. The mixture was slowly warmed to RT and then stirred for 18 h at RT. MeOH was then added and volatiles were removed in vacuo. The resulting residue was dissolved in DMF and filtered thought a pad of silica eluting with 10% 2M NH3/MeOH in DCM. The residue was further purified by column chromatography (Si-PCC, gradient 0-10% 2M NH3/MeOH in DCM) and then loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH and the product eluted with 2M NH3/MeOH. The product containing fractions were combined and concentrated in vacuo affording 1-(1-Benzylazepan-4-yl)ethanol (600 mg, 65%). 1H NMR (CDCl3, 400 MHz): δ 7.38-7.19 (5H, m), 3.99-3.47 (5H, m), 2.92-2.38 (4H, m), 2.01-1.51 (6H, m), 1.19 (3H, m)

Provenance & Evidence