Tetrabutylammonium Fluoride → [5-(4-{1-ethyl-1-[4-(1-hydroxy-cyclopentylethynyl)-3-methyl-phenyl]-propyl}-2-methyl-phenyl)-pyridin-2-yl]-acetic Acid Methyl Ester

HRID 546976Notes

Reaction equation

HRID 546976 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][O:20][C:21](=[O:60])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][C:32]([C:35]([CH2:57][CH3:58])([C:38]3[CH:43]=[CH:42][C:41]([C:44]#[C:45][C:46]4([O:51][Si](C)(C)C)[CH2:50][CH2:49][CH2:48][CH2:47]4)=[C:40]([CH3:56])[CH:39]=3)[CH2:36][CH3:37])=[CH:31][C:30]=2[CH3:59])=[CH:25][N:24]=1>O1CCCC1>[CH3:19][O:20][C:21](=[O:60])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][C:32]([C:35]([CH2:36][CH3:37])([C:38]3[CH:43]=[CH:42][C:41]([C:44]#[C:45][C:46]4([OH:51])[CH2:50][CH2:49][CH2:48][CH2:47]4)=[C:40]([CH3:56])[CH:39]=3)[CH2:57][CH3:58])=[CH:31][C:30]=2[CH3:59])=[CH:25][N:24]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57709210[5-(4-{1-ethyl-1-[3-methyl-4-(1-trimethylsilanyloxy-cyclopentylethynyl)-phenyl]-propyl}-2-methyl-phenyl)-pyridin-2-yl]-acetic Acid Methyl Ester

Product 1

HCID 57708941[5-(4-{1-ethyl-1-[4-(1-hydroxy-cyclopentylethynyl)-3-methyl-phenyl]-propyl}-2-methyl-phenyl)-pyridin-2-yl]-acetic Acid Methyl EsterYield 48.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran (0.0466 mL, 0.0466 mmol) was added to a solution of [5-(4-{1-ethyl-1-[3-methyl-4-(1-trimethylsilanyloxy-cyclopentylethynyl)-phenyl]-propyl}-2-methyl-phenyl)-pyridin-2-yl]-acetic acid methyl ester (Example 95-(1); 18.1 mg, 0.031 mmol) in tetrahydrofuran (0.050 mL), and the mixture was stirred for 30 minutes. The reaction mixture was purified by silica gel chromatography (25% ethyl acetate/hexane) to give the title compound (7.6 mg, 47%).

Workup

  1. customThe reaction mixture was purified by silica gel chromatography (25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-988393d977b34d84bd4a1d2302248708
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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