Water → HCID 67397694, compound

HRID 70655Notes

Reaction equation

HRID 70655 reaction equation
C([SnH](CCCC)CCCC)CCC.N(C(C)(C)C#N)=NC(C)(C)C#N.C(SC)(=S)O[CH:28]([C:30]1[C:31]([O:65][CH3:66])=[N:32][C:33](/[C:36](/[C:55]2[CH:60]=[CH:59][C:58]([C:61]([CH3:64])([CH3:63])[CH3:62])=[CH:57][CH:56]=2)=[CH:37]/[C@H:38]2[CH2:42][CH2:41][C:40](=[O:43])[N:39]2[CH2:44][C:45]2[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][C:46]=2[O:53][CH3:54])=[CH:34][CH:35]=1)[CH3:29].O>C1(C)C=CC=CC=1>[C:61]([C:58]1[CH:59]=[CH:60][C:55](/[C:36](/[C:33]2[CH:34]=[CH:35][C:30]([CH2:28][CH3:29])=[C:31]([O:65][CH3:66])[N:32]=2)=[CH:37]\[C@@H:38]2[N:39]([CH2:44][C:45]3[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][C:46]=3[O:53][CH3:54])[C:40](=[O:43])[CH2:41][CH2:42]2)=[CH:56][CH:57]=1)([CH3:63])([CH3:62])[CH3:64]

Participants

6

Reactant 4

HCID 962WaterHCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 86658011HCID 86658011, compound

Product 1

HCID 67397694HCID 67397694, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

Tributyltin hydride (91 μL) and azobisisobutyronitrile (8.5 mg) were added to a solution of O-[1-(6-{(E)-1-(4-tert-butylphenyl)-2-[(2R)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidin-2-yl]ethenyl}-2-methoxypyridin-3-yl)ethyl] S-methyl carbonodithioate (109 mg) in toluene (2 mL), and the mixture was stirred at 120° C. for 30 minutes. Water was added to the reaction solution, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to give (5R)-5-[(E)-2-(4-tert-butylphenyl)-2-(5-ethyl-6-methoxypyridin-2-yl)ethenyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one as a colorless oil (65 mg).

Workup

  1. extractionfollowed by extraction with chloroform
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customThe solvent was then evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-86061efff23f4881bc33545b3bf7e433
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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