Phenol → HCID 59908685, compound

Participants

Reaction Steps

N-(3,4-Dimethoxybenzenesulfonyl)-[(2S,4R)-4-hydroxy-2-pyrrolidinecarboxylic acid] methyl ester (8) (1.00 g, 2.90 mmol), phenol (0.41 g, 4.34 mmol) and triphenylphosphine (1.14 g, 4.34) are combined in THF (10 mL). The mixture is cooled in an ice-bath and diethyl azodicarboxylate (0.76 g, 4.34 mmol) is added dropwise over 30 minutes. The reaction is allowed to warm to ambient temperature with overnight stirring. The reaction mixture is concentrated at reduced pressure and treated with ether. The mixture is decanted and the organic extract is concentrated. The residue is purified via silica gel chromatography (40% ethyl acetate in hexanes) affording the desired product as a solid. CIMS: MH+ 422

Provenance & Evidence