Phthalimide → tert-butyl [1-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-(methylsulfanyl)butan-2-yl]carbamate

Participants

Reaction Steps

To a solution of tert-butyl [1-hydroxy-4-(methylsulfanyl)butan-2-yl]carbamate (18.5 g, 84.5 mmol) in THF (400 mL) was added phthalimide (14.9 g, 0.101 mol) and triphenylphosphine (26.9 g, 0.101 mol) under a nitrogen atmosphere. Diethylazodicarboxylate (27.3 g, 0.135 mol) was added dropwise at room temperature. After 2 hours, the reaction mixture was concentrated under reduced pressure, and the residue was purified by chromatography on silica gel to give tert-butyl {1-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-(methylsulfanyl)butan-2-yl}carbamate. MS ESI calc'd. for C18H25N2O4S [M+H]+ 365. found 365. 1H NMR (400 MHz, CDCl3) δ 7.87-7.71 (m, 4H), 4.72 (s, 1H), 4.16-4.07 (m, 1H), 3.76 (d, J=6.6 Hz, 2H), 2.68-2.54 (m, 2H), 2.13 (s, 3H), 1.75-1.55 (m, 2H), 1.35 (s, 9H).

Provenance & Evidence