Sodium cyanoborohydride → Tert-butyl 4-(2-(tert-butoxycarbonyl)hydrazinyl)piperidine-1-carboxylate

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Reaction Steps

To tert-butyl 4-[(tert-butoxycarbonyl)hydrazono]piperidine-1-carboxylate (15.7 g; 50.1 mmol; 1 eq.) in water (78.5 mL) and glacial acetic acid (78.5 mL) is added sodium cyanoborohydride (3.15 g; 50.1 mmol; 1 eq.) and the reaction mixture is stirred at rt overnight. The solvents are removed to near dryness and the product is extracted with AcOEt. The combined organic phase is washed with NaOH (1 M), dried over MgSO4, filtered and concentrated to afford: 14.1 g (89%) of the title compound. 1H NMR (300 MHz, DMSO): δ 8.22 (s, 1H), 4.61-4.14 (m, 1H), 3.81-3.55 (m, 2H), 3.08-2.67 (m, 2H), 1.73-1.50 (m, 2H), 1.38 (s, 18H), 1.22-0.98 (m, 2H).

Provenance & Evidence