Triphenylphosphine → 1-(3-tert-Butyl-isoxazol-5-yl)-3-methyl-3-(tetrahydro-pyran-4-sulfonyl)-pyrrolidin-2-one

Participants

Reaction Steps

To a solution of di-tert-butyl azodicarboxylate (0.126 g; 0.546 mmol) in methylene chloride (2.5 mL) was added triphenylphosphine (0.143 g; 0.546 mmol). The mixture was stirred 30 minutes and N-(3-tert-butyl-isoxazol-5-yl)-4-hydroxy-2-methyl-2-(tetrahydro-pyran-4-sulfonyl)-butyramide (0.212 g; 0.546 mmol) was added. After 3 hours the volatiles were removed in vacuo. The residue was purified by silica gel chromatography using ethyl acetate and hexanes as the eluent. Removal of the volatiles from the product-rich fractions provided 0.105 g of the solid product. 1H NMR (CDCl3) δ 6.41 (s, 1H), 4.09 (m, 4H), 3.85 (m, 1H), 3.49 (m, 2H), 3.24 (m, 1H), 2.25-1.86 (m, 5H), 1.75 (s, 3H), 1.35 (s, 9H). MS (ESI): m/e 371 (M+H).

Provenance & Evidence