反応 #2267087

反応方程式

iodine

(rac)-2-(2,3,5,6-tetrahydro[1,4]oxazino[2,3,4-hi]indol-6-ylmethyl)-1H-isoindole-1,3(2H)-dione

iodine

iodine

→

title compound

(rac)-2-[(8-iodo-2,3,5,6-tetrahydro[1,4]oxazino[2,3,4-hi]indol-6-yl)methyl]-1H-isoindole-1,3(2H)-dione

溶媒

CHCl3

CHCl3

CHCl3

CHCl3

反応条件

後処理

1. 1
   workup.STIRRINGThe mixture was stirred at rt for 4 h
2. 2
   workup.STIRRINGAfter stirring for another 2 h
3. 3
   ろ過the mixture was filtered through a pad of celite
4. 4
   洗浄washed with CHCl3
5. 5
   洗浄The filtrate was washed with Na2SO3 solution
6. 6
   乾燥dried (MgSO4)
7. 7
   ろ過After filtration
8. 8
   濃縮the filtrate was concentrated in vacuo to dryness

実験手順

To a suspension of (rac)-2-(2,3,5,6-tetrahydro[1,4]oxazino[2,3,4-hi]indol-6-ylmethyl)-1H-isoindole-1,3(2H)-dione (0.081 g, 0.253 mmol) and silver trifluoroacetate (0.059 g, 0.266 mmol) in CHCl3 (2.0 mL) was added a solution of iodine (0.067 g, 0.266 mmol) in CHCl3 (8.0 mL) dropwise at rt. The mixture was stirred for 68 h. Silver trifluoroacetate (0.03 g, 0.136 mmol) and solution of iodine (0.035 g, 0.136 mmol) in CHCl3 (6.0 mL) were added. The mixture was stirred at rt for 4 h and added again silver trifluoroacetate (0.02 g, 0.09 mmol) and solution of iodine (0.025 g, 0.10 mmol) in CHCl3 (5.0 mL). After stirring for another 2 h, the mixture was filtered through a pad of celite and washed with CHCl3. The filtrate was washed with Na2SO3 solution and dried (MgSO4). After filtration, the filtrate was concentrated in vacuo to dryness and the residue was subjected to prep TLC (EtOAc/hexane, 1:2) to give 0.046 g (41%) of light yellow oil as the title compound: 1H NMR (400 MHz, CDCl3) δ 7.81-7.78 (m, 2 H), 7.69-7.65 (m, 2 H), 6.98 (s, 1 H), 6.86 (s, 1 H), 4.34-4.29 (m, 2 H), 3.91-3.80 (m, 2 H), 3.62-3.58 (m, 1 H), 3.24-3.14 (m, 2 H), 3.04-3.00 (m, 1 H), 2.97-2.92 (m, 1 H); MS (EI) m/z 447 (M++H).

出典