Water → Isopropyl 5-(2-aminoethyl)thiophene-2-carboxylate

Participants

Reaction Steps

Water (0.1 mL) and triphenylphosphine (288 mg, 1.1 mmol) were added sequentially to a solution of the azide from step 3 (239 mg, 1.0 mmol) in THF (2.0 mL) and the reaction was stirred at room temperature overnight. The solvent was removed under a stream of nitrogen and then 1.0 N aqueous HCl (7.5 mL) was added. The mixture was extracted with EtOAc (2×5 mL). The aqueous phase was basified with 2.0 M aqueous NaOH (5 mL). The mixture was extracted with EtOAc (3×10 mL) and these extracts were dried (Na2SO4), filtered and concentrated in vacuo to afford 175 mg (82%) of the title compound.

Provenance & Evidence