Triphenylphosphine → HCID 22225460, compound

Participants

Reaction Steps

To a mixture of 2-hydroxymethyl-heptanoic acid benzyloxyamide (5.36 g, 20.23 mmol) and triphenylphosphine (5.31 g, 20.23 mmol) in THF (200 mL) at 0° C. was added dropwise diethyl azodicarboxylate (3.3 mL, 20.23 mmol). The reaction was stirred at room temperature overnight. The reaction was then quenched by adding water (200 mL). The aqueous layer was extracted with EtOAc (200 mL×2). The combined organic layer was washed with brine, and dried over MgSO4. After removing the solvent under vacuum, the residue was purified by flash column chromatography (hexane:EtOAc 5/1) to provide the title compound (4.68 g, 94%). 1H NMR (400 MHz, CHCl3) δ 7.35–7.25 (m, 5H), 4.87 (s, 2H), 3.28 (t, J=4.85 Hz, 1H), 2.84 (q, J=2.35 Hz, 1H), 2.77 (m, 1H), 1.62 (m, 1H), 1.36 (m, 1H), 1.25 –1.16 (m, 6H), 0.88 (t, J=6.9 Hz, 3H). MH+ 248.

Provenance & Evidence