Phthalimide → HCID 86761371, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of tert-butyl [1-(hydroxymethyl)tricyclo[3.3.1.03,7]non-3-yl]carbamate (as obtained in step VI preparation 3) (0.67 g, 2.5 mmol) in toluene (10 mL) was added phthalimide (0.52 g, 3.5 mmol), triphenylphosphine (1.05 g, 4.0 mmol), and diisopropylazodicarboxylate (0.8 mL, 4.0 mmol). The reaction mixture was heated to 90° C. for 4 h. The volatiles were removed under reduced pressure and the residue was purified by column chromatography to obtain tert-butyl [2-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]hexahydro-2,5-methanopentalen-3a(1H)-yl]carbamate (0.45 g) as a viscous liquid in 46% yield. m/z (M+1) 397; 1H NMR (CDCl3) 300 MHz δ 7.90-7.80 (m, 2H), 7.77-7.68 (m, 2H), 4.75 (s (br), 1H), 3.60 (s, 2H), 2.47-2.35 (m, 1H), 2.36-2.29 (m, 1H), 2.02-1.84 (m, 4H), 1.77-1.65 (m, 2H), 1.64-1.35 (m, 5H), 1.41 (s, 9H), 1.34-1.24 (m, 1H).

Provenance & Evidence