Triphenylphosphine → HCID 18626481, compound

Participants

Reaction Steps

According to the method of Example 32, Step 1, 3-[1-(triphenylmethyl)-1H-imidazole-4-yl]propanol (see for example, J. Med. Chem., 1996;39: 1220-1226) (2.58 g, 7 mmol) was coupled to 6-hydroxy tetralone (1.30 g, 7 mmol) with diethylazodicarboxylate (1.26 mL, 8 mmol) and triphenylphosphine (2.10 g, 8 mmol) in 10 mL of dry THF to afford, after chromatography (SiO2, 50% EtOAc in hexanes), 2.73 g of a 1:1 mixture of the title compound and Ph3PO as determined by HPLC analysis (C18, 0.1% TFA in H2O:0.1% TFA in AcCN gradient 80:20 to 20:80): title compound, retention time=15.87 minutes (48.2%); Ph3PO, retention time=13.12 minutes (50.1%). CI-MS m/e 279 (Ph3PO), 513 (M++1).

Provenance & Evidence