tert-Butyl 3-(hydroxymethyl)piperidine-1-carboxylate → 1-Boc-piperidine-3-carboxaldehyde

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Reaction Steps

To a solution of Example 1B (5 g, 23.22 mmol) in dichloromethane (50 mL) was added pyridinium chlorochromate (10.01 g, 46.4 mmol) and the mixture was stirred for 12 hours. The mixture was filtered and concentrated to afford crude product which was purified by column chromatography (silica gel, 40% ethyl acetate in hexane) to afford the title compound. 1H NMR (300 MHz, CDCl3): δ 1.44 (s, 9H), 1.5-1.54 (m, 1H), 1.66-1.69 (m, 2H), 1.9-2.0 (m, 1H), 2.38-2.46 (m, 1H), 3.04-3.12 (m, 1H), 2.38-3.36 (m, 1H), 3.6-3.68 (m, 1H), 3.88-4.0 (m, 1H), 9.7 (s, 1H).

Provenance & Evidence