Triphenylphosphine → HCID 12132432, compound

Participants

Reaction Steps

A stirred solution of 4-hydroxyindole (1.33 g, 10.0 mmol), (R)-(+)-1-(t-butoxycarbonyl)-2-pyrrolidinemethanol (4.02 g, 20.0 mmol) and triphenylphosphine (5.3 g, 20.0 mmol) in THF is treated with diethyl azodicarboxylate (3.2 mL, 20 mmol), stirred for 3 h at room temperature and concentrated in vacuo. The resultant residue is treated with EtOAc and filtered through a pad of silica gel. The filtrate is concentrated to give a residue which is purified by chromatography (silica gel, EtOAc:hexanes, 15:80) to afford the title compound as a white solid, 1.08 g, mp 146-147° C.; identified by NMR and mass spectral analyses.

Provenance & Evidence