Triphenylphosphine → (3S)-(+)-1-Benzyl-3-aminopyrrolidine

Participants

Reaction Steps

The compound (3S)-1-benzyl-3-azidopyrrolidine (0.9 g, 4.5 mM) was dissolved in a mixture of tetrahydrofuran (36.0 ml) and water (7.0 ml). To it, triphenylphosphine (2.3 g, 8.9 mM) was added and the reaction mixture was refluxed for 7 hours. The reaction mixture was cooled to room temperature and tetrahydrofuran was evaporated under vacuum. The residue was taken in water (50.0 ml) and the pH was adjusted to about 2 and washed with chloroform. The pH of the aqueous solution was adjusted to about 12-13 with 1N sodium hydroxide and extracted with chloroform. The chloroform layer was washed with water and brine solution. It was further dried over anhydrous sodium sulphate and concentrated to give the title compound. Yield=62% (0.5 g, 2.8 mM).

Provenance & Evidence