Tetrabutylammonium Fluoride → (5R)-5-{(E)-2-(4-tert-butylphenyl)-2-[5-(4-hydroxybutyl)-6-methoxypyridin-2-yl]ethenyl}-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one

HRID 70663Notes

Reaction equation

HRID 70663 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]1[CH:32]=[CH:33][C:34](/[C:39](/[C:58]2[CH:63]=[CH:62][C:61]([C:64]([CH3:67])([CH3:66])[CH3:65])=[CH:60][CH:59]=2)=[CH:40]/[C@@H:41]2[N:45]([CH2:46][C:47]3[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][C:48]=3[O:55][CH3:56])[C:44](=[O:57])[CH2:43][CH2:42]2)=[N:35][C:36]=1[O:37][CH3:38])(C(C)(C)C)(C)C>O1CCCC1>[C:64]([C:61]1[CH:62]=[CH:63][C:58](/[C:39](/[C:34]2[CH:33]=[CH:32][C:31]([CH2:30][CH2:29][CH2:28][CH2:27][OH:26])=[C:36]([O:37][CH3:38])[N:35]=2)=[CH:40]\[C@@H:41]2[N:45]([CH2:46][C:47]3[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][C:48]=3[O:55][CH3:56])[C:44](=[O:57])[CH2:43][CH2:42]2)=[CH:59][CH:60]=1)([CH3:67])([CH3:65])[CH3:66]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67398640HCID 67398640, compound

Product 1

HCID 67397159(5R)-5-{(E)-2-(4-tert-butylphenyl)-2-[5-(4-hydroxybutyl)-6-methoxypyridin-2-yl]ethenyl}-1-(2,4-dimethoxybenzyl)pyrrolidin-2-oneYield 86.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of tetra-n-butylammonium fluoride in tetrahydrofuran (1 mL) was added to a solution of (5R)-5-[(E)-2-[5-(4-{[tert-butyl(dimethyl)silyl]oxy}butyl)-6-methoxypyridin-2-yl]-2-(4-tert-butylphenyl)ethenyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one (140 mg) in tetrahydrofuran (4 mL), and the mixture was stirred at room temperature for three hours. The solvent was evaporated from the reaction solution under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→0:10) to give (5R)-5-{(E)-2-(4-tert-butylphenyl)-2-[5-(4-hydroxybutyl)-6-methoxypyridin-2-yl]ethenyl}-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one as a colorless oil (101 mg, 86%).

Workup

  1. customThe solvent was evaporated from the reaction solution under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→0:10)

Sources & evidence

ORD record
ord-744a96d9244e4c00bcdb125485da487d
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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