Tributylstannane → 5-Acetyl-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,7'-indolizidine]

HRID 1274237Notes

Reaction equation

HRID 1274237 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

Reactant 2

HCID 5948TributylstannaneHCID 221209261-Acetyl-6-bromo-5-[(1,2,3,5,6,8a-hexahydroindolizin-7-yl)methoxy]indoline

Product 1

HCID 1317221945-Acetyl-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,7'-indolizidine]Yield 77.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

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.

Workup

  1. temperatureat reflux for 6 h
  2. temperaturecooled
  3. extractionextracted with dil. HCl
  4. extractionextracted with chloroform
  5. extractionThe organic extract
  6. dry with materialwas dried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-a4fc60b2cc4f479693ca8a9f1926a805
Source dataset
uspto-grants-2000_12
Patent number
US06156783

Reaction notes

Loading…