Triphenylphosphine → HCID 66653592, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve 4-((R)-3-hydroxy-pyrrolidin-1-yl)-benzonitrile (188 mg, 1.00 mmol), triphenylphosphine (393 mg, 1.50 mmol) and 3-hydroxy-benzoic acid methyl ester (228 mg, 1.5 mmol) into 10 mL of dry THF under Ar. Cooled to 4° C. Add DEAD (0.26 mL, 1.50 mmol) in a drop-wise fashion. Stir mixture with warming to room temperature overnight. LC-MS analysis indicates the desired intermediate. Concentrate the mixture to dryness. Dissolve residue into CH2Cl2 and apply to a 2 mm SiO2 prep plate. Elute with 50% EtOAc/hexanes to give 113 mg of slightly impure 3-[(S)-1-(4-cyano-phenyl)-pyrrolidin-3-yloxy]-benzoic acid methyl ester.

Provenance & Evidence