Tributylstannane → tert-Butyl 5-(trifluoromethyl)spiro[indoline-3,3'-pyrrolidine]-1'-carboxylate

HRID 1411318Notes

Reaction equation

HRID 1411318 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[NH:12][CH2:13][C:14]1[CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH:18]=1.C([SnH](CCCC)CCCC)CCC.N(C(C)(C)C#N)=NC(C)(C)C#N>C1C=CC=CC=1>[F:9][C:8]([F:11])([F:10])[C:6]1[CH:7]=[C:2]2[C:14]3([CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15]3)[CH2:13][NH:12][C:3]2=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 90449914tert-butyl 3-(((2-bromo-4-(trifluoromethyl)phenyl)amino)methyl)-2,5-dihydro-1H-pyrrole-1-carboxylate

Product 1

HCID 90449647tert-Butyl 5-(trifluoromethyl)spiro[indoline-3,3'-pyrrolidine]-1'-carboxylateYield 42.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

tert-Butyl 3-(((2-bromo-4-(trifluoromethyl)phenyl)amino)methyl)-2,5-dihydro-1H-pyrrole-1-carboxylate (6.46 g, 15.3 mmol) was dissolved in benzene (300 mL). Thereafter, tributyltin hydride (6.02 mL, 23.0 mmol) and azobisisobutyronitrile (380 mg, 2.31 mmol) were added to the above obtained solution at room temperature, and the thus obtained mixture was then stirred for 15 hours while heating under reflux. Thereafter, the reaction solution was concentrated in vacuo, and the obtained residue was then purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to obtain tert-butyl 5-(trifluoromethyl)spiro[indoline-3,3′-pyrrolidine]-1′-carboxylate (2.21 g, 42%) in the form of a colorless amorphous product.

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux
  3. concentrationThereafter, the reaction solution was concentrated in vacuo
  4. customthe obtained residue was then purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-f9ad2439c7b84deb84947f4d54b3e6d9
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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