Hydrogen Bromide → HCID 86717584, compound

Participants

Reaction Conditions

Reaction Steps

To a light orange suspension of 1-((7-((benzyloxy)methyl)-2-oxo-1-oxa-3-azaspiro[4.5]decan-7-yl)methyl)-1H-benzo[d]imidazole-6-carbonitrile (0.120 g, 0.279 mmol) in 1,4-dioxane (2.157 mL) was added concentrated hydrobromic acid (0.631 mL, 5.57 mmol). The reaction mixture was heated at 70° C. for 17 h. The reaction was then cooled to RT. Next, 6N NaOH was added till the pH was adjusted to 13 and then the mixture extracted with EtOAc (2×10 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated. The compound was loaded onto florisil and purified using silica gel chromatography: 1-5% methanol/dichloromethane (25 min), 4 g silica. The product eluted early from 2-10 minutes. Next, the compound was loaded onto florisil and purified using silica gel chromatography: 1-10% methanol/dichloromethane (30 min), 12 g silica. The product did not elute cleanly but did yield 1-{[(5S,7R)-7-(hydroxymethyl)-2-oxo-1-oxa-3-azaspiro[4.5]dec-7-yl]methyl}-1H-benzimidazole-6-carbonitrile (70% pure, 62 mg, 46% yield). MS (m/z) 341.0 (M+H+).

Provenance & Evidence