Sodium Carbonate → (S)-benzyl 3-(ethylamino)piperidine-1-carboxylate

Participants

Reaction Steps

A solution of (S)-benzyl 3-(tert-butoxycarbonylamino)piperidine-1-carboxylate (300 mg, 0.82 mmol) in 1,4-dioxane (2.5 mL) was treated with dioxane. HCl (5 mL) and the solution was stirred at rt 1 h. The solvent was reduced in vacuo to afford a residue which was then dissolved in water (5 mL). The aqueous solution was treated with solid Na2CO3 and the aqueous solution was extracted with EtOAc (3×15 mL). The combined organic layer was dried over Na2SO4, concentrated in vacuo to yield titled intermediate (217 mg, 92%), which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3): δ 7.36-7.26 (m, 5H), 5.13 (s, 2H), 4.20-3.82 (m, 2H), 2.94-2.60 (m, 5H), 1.94-1.92 (m, 1H), 1.69-1.68 (m, 1H), 1.47-1.28 (m, 3H), 1.09 (t, J=6.8 Hz, 3H). ES-MS: m/z [M+1]=263.

Provenance & Evidence