Isobutylamine → tert-Butyl 4-(isobutylamino)piperidine-1-carboxylate

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Reaction Steps

To 10% Pd/C (3.0 g, 10% wt), under nitrogen, is added a solution of the 1-Boc-4-piperidone (30 g, 150.6 mmol, 1.0 eq.) and isobutylamine (11.2 g, 180.3 mmol, 1.2 eq) in ethanol (300 ml). This is hydrogenated for 1.5 h at 65 psi using a Parr hydrogenator. The catalyst is removed by filtration through Celite. Solvent is removed under vacuum to give 4-isobutylamino-piperidine-1-carboxylic acid tert-butyl ester as a colourless oil (31.2 g) with >98% purity. Mass spectrum (LCMS) Rt=2.79 (6 min gradient) (M++1) 257.2; 1H NMR (CDCl3): δ=4.01 (2H, brs), 2.82-2.75 (2H, m), 2.61-2.54 (1H, m), 2.43 (2H, d), 1.85-1.81 (2H, m), 1.76-1.67 (1H, m), 1.56 (1H, br s), 1.45 (9H, s), 1.31-1.18 (2H, m), 0.91 (6H, d).

Provenance & Evidence