Hydrochloric Acid → Benzyl 4-(methoxycarbonylamino)piperidine-1-carboxylate

Participants

Reaction Steps

To a solution of 1.0 g (3.9 mmol) of (1-benzyloxycarbonyl-piperidin-4-yl)isocyanate from Example 64, Step A in 10 mL of methanol was added 5 mg (cat) of DMAP. The reaction was stirred under nitrogen at rt for 24 h and then poured into water containing 2 mL of 2 N hydrochloric acid and was extracted twice with ethyl acetate. The organic layers were each washed with a portion of brine, dried over sodium sulfate, combined and concentrated to give 1.4 g of the crude title compound which can be used directly in subsequent reactions. 1H NMR (400 MHz, CDCl3): δ 1.32 (m, 2H), 1.92 (br d, J=10, 4H), 2.91 (v br t, 2H), 3.66 (br s, 3H+1H), 4.10 (m, 2H), 4.58 (br s, 1H), 5.09 (s, 2H), 7.33 (m, 5H).

Provenance & Evidence