(R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate → (r)-5-Tert-butyl-1-((tetrahydrofuran-2-yl)methyl)pyridin-2(1h)-imine

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A mixture of Example 59B (0.5 g, 3.3 mmol), (R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate (0.9 g, 3.6 mmol), and tetraethylammonium iodide (0.4 g, 1.6 mmol) in N,N-dimethylformamide (1.0 mL) was heated at 95° C. for 16 hours. After cooling to ambient temperature, the mixture was quenched with saturated NaHCO3 (10 mL) and extracted with dichloromethane (3×30 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to provide the title compound. LCMS (APCI+) m/z 235 (M+H)+.

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