Water → tert-Butyl 4-(2-aminoethyl)piperidine-1-carboxylate

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Reaction Steps

To a solution of 2-(N-Boc-4-piperidinyl)ethylazide (19.3 g, 0.076 moles) in THF (400 ml)/H2O (195 ml) was added triphenylphosphine (80.0 g, 0.305 moles) in one portion at room temperature. This was stirred at room temperature 3 hours and the organic solvents were then removed in vacuo. The residue was acidified to pH 2 with 10% KHSO4 solution and this was extracted 4×100 ml portions of EtOAc. The organic extract was extracted with 2×100 ml portions of 10% KHSO4 and the aqueous phases were combined and the pH was adjusted to 10 with 2N NaOH. This solution was extracted with 4×200 ml portions of CH2Cl2. These were combined, dried (MgSO4) and the solvent was removed to give 1-2 as an oil. Rf 0.3 (silica gel, eluting with 10% CH3OH in CHCl3 /NH3).

Provenance & Evidence