Hydrochloric Acid → 7'-Bromo-4-methoxy-3',4'-dihydro-1'H-spiro[cyclohexane-1,2'-naphthalen]-1'-imine

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Reaction Steps

To N-(7′-bromo-4-methoxy-3′,4′-dihydro-1′H-spiro[cyclohexane-1,2′-naphthalene]-1′-ylidene)-2-methylpropane-2-sulfinamide (Intermediate 13, 0.610 g, 1.43 mmol) under N2 (g) was added HCl (4 M in 1,4-dioxane, 3.58 mL, 14.3 mmol). The mixture was stirred at r.t. for 45 min and was then concentrated. DCM (approx. 2 mL) was added followed by Et2O. A solid formed and was filtered off and washed with Et2O. The solid was dissolved in DCM. NaHCO3 (sat. aq.) was added and the mixture was poured into a phase separator. The organic phase was collected and concentrated to give the title compound (0.35 g, 76% yield): MS (EI) m/z 321 M+.

Provenance & Evidence