Ammonia → 3,3-Diphenyl-3,4,5,6-tetrahydropyridin-2-ol

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Reaction Steps

The product of Example 1B (14.4 g, 49.1 mmol) and 7 M ammonia in methanol (150 mL) were added to solvent-washed Raney®-nickel (72.0 g, 1227 mmol), and the mixture was stirred at room temperature for 24 hours under hydrogen (30 pounds per square inch). The mixture was filtered through a nylon membrane, and the filtrate was concentrated. The residue was dissolved in dichloromethane/methanol (1:1) and filtered through diatomaceous earth to remove a greenish residue. The filtrate was concentrated to obtain a solid which was slurried in methanol, filtered, and dried to obtain the title compound. MS (DCI+) m/z 251 (M+H)+.

Provenance & Evidence