Tributylstannane → 5-Acetyl-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,7'-indolizidine]
Reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:14][CH2:15][C:16]3[CH2:17][CH2:18][N:19]4[CH:23]([CH:24]=3)[CH2:22][CH2:21][CH2:20]4)=[C:10](Br)[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C([SnH](CCCC)CCCC)CCC>C1C=CC=CC=1>[C:1]([N:4]1[C:12]2[CH:11]=[C:10]3[C:16]4([CH2:15][O:14][C:9]3=[CH:8][C:7]=2[CH2:6][CH2:5]1)[CH2:24][CH:23]1[N:19]([CH2:20][CH2:21][CH2:22]1)[CH2:18][CH2:17]4)(=[O:3])[CH3:2]Participants
4
Procedure
1-Acetyl-6-bromo-5-[(1,2,3,5,6,8a-hexahydroindolizin-7-yl)methoxy]indoline (D3) (0.118 g, 0.3 mmol) and α,α'-azoisobutyronitrile (0.04 g) were stirred at reflux under Ar in benzene (40 ml) as tributyltin hydride (0.24 ml, 0.9 mmol) was added dropwise in benzene (10 ml) over 10 min. The mixture was stirred at reflux for 6 h, cooled, and extracted with dil. HCl. The extract was basified with saturated K2CO3, and extracted with chloroform. The organic extract was dried (Na2SO4) and evaporated to give the title compound (0.073 g, 77%) as a brown gum. NMR showed a mixture of two isomers.