Reaktion #10055

Reaktionsgleichung

1,8-Diazabicyclo[5,4,0]undec-7-ene

4-(aminomethyl)-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione hydrochloride

t-butylisocyanate

→

product

Ausbeute 51.0%

1-tert-Butyl-3-[2-(2,6-dioxo-piperidin-3-yl),1,3-dioxo-2,3-dihydro-1H-isoindol-4-ylmethyl]-urea

Ausbeute 51.0%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGAfter stirring for 1 hour
2. 2
   workup.STIRRINGThe mixture was stirred at room temperature for 17 hours
3. 3
   SonstigeThe solvent was removed in vacuo
4. 4
   workup.DISSOLUTIONthe residue was dissolved in dichloromethane (70 ml)
5. 5
   Waschenwashed with 0.1 N HCl (20 ml), water (20 ml), brine (20 ml)
6. 6
   Sonstigedried
7. 7
   SonstigeThe solvent was removed in vacuo
8. 8
   Sonstigethe resulting solid was recrystallized from ethanol/isopropyl ether

Vorschrift

1,8-Diazabicyclo[5,4,0]undec-7-ene (0.28 g, 1.9 mmol) was added to stirred suspension of 4-(aminomethyl)-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione hydrochloride (0.6 g, 1.9 mmol) in acetonitrile (50 ml). After stirring for 1 hour, t-butylisocyanate (0.21 g, 2 mmol) was added. The mixture was stirred at room temperature for 17 hours. The solvent was removed in vacuo and the residue was dissolved in dichloromethane (70 ml) and washed with 0.1 N HCl (20 ml), water (20 ml), brine (20 ml) and dried. The solvent was removed in vacuo and the resulting solid was recrystallized from ethanol/isopropyl ether to give 0.36 g (51%) of the product: mp 186–188° C.; 1H NMR (DMSO-d6) δ 11.04 (s, 1H), 7.77–7.59 (m, 3H), 6.17 (t, J=6.2 Hz, 1H), 5.86 (s, 1H), 508–5.01 (dd, J=5.4 and 12.4 Hz, 1H), 4.49 (d, J=6.0 Hz, 2H), 2.82–2.73 (m, 1H), 2.54–2.40 (m, 2H), 1.98–1.94 (m, 1H), 1.12 (s, 9H); 13C NMR (DMSO-d6) δ 172.33, 169.39, 167.11, 166.59, 156.85, 140.72, 134.20, 132.99, 131.06, 126.54, 121.20, 48.69, 48.37, 37.89, 30.46, 28.88, 21.53; Anal. Calcd. For C19H22N4O5+0.2 water: C, 58.51; H, 5.79; N, 14.37. Found: C, 58.86; H, 6.15; N, 14.24.

Quelle