7-amino-4-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-2-methyl-2,3-dihydro-1H-isoindol-1-one → 7-amino-4-(1,4-dioxaspiro[4.5]dec-8-yl)-2-methyl-2,3-dihydro-1H-isoindol-1-one

Participants

Reaction Steps

To a solution of 7-amino-4-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-2-methyl-2,3-dihydro-1H-isoindol-1-one (1.7 g, 5.7 mmol) in EtOH (100 mL) was added palladium 10% wt on activated carbon (0.60 g, 0.57 mmol). The reaction mixture was evacuated and purged with hydrogen (3×) and stirred over night at rt. The reaction mixture was filtered through a pad of celite and concentrated in vacuo to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ 7.04 (d, J=8.34 Hz, 1H), 6.52 (d, J=8.08 Hz, 1H), 5.85 (s, 2H), 4.34 (s, 2H), 3.86-3.89 (m, 4H), 2.98 (s, 3H), 2.42-2.48 (m, 1H), 1.52-1.80 (m, 8H); MS (ES+): m/z: 303.1516 [MH+]. HPLC: tR=1.21 min (UPLC TOF MS: polar—3 min).

Provenance & Evidence