Triphenylphosphine → HCID 15485233, compound

Participants

Reaction Steps

2.513 g (10 mmol) of (S)-(-)-2-(t-Butoxycarbonylamino)-3-phenyl-1-propanol was added at once to a magnetically stirred solution of 2.885 g (11 mmol) triphenylphosphine in tetrahydrofuran (100 mL) at 0° C. Thereafter 1.9 mL (12 mmol) diethyl azodicarboxylate was added dropwise over 3 minutes while the temperature was maintained between 0 and 5° C. This was immediately followed by adding a solution of 2.14 g (10 mmol) of 4-hydroxy-4-(3-methoxy-thiophen-2-yl)-piperidine in 100 mL tetrahydrofuran. The reaction mixture was stirred at ambient temperature overnight, evaporated in vacuo to dryness and the residue flash chromatographed on 300 g silica gel using chloroform as eluant yielding 2.6 g of the title compound as a faintly yellow dense oil.

Provenance & Evidence