Styrene → 2-(1-Allylpyrrolidin-3-yl)-6-methoxypyridine

HRID 2178512Notes

Reaction equation

HRID 2178512 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[N:4]=1)=[CH2:2].CO[CH2:13][N:14](C[Si](C)(C)C)[CH2:15][CH:16]=[CH2:17].[CH2:23]=CC1C=CC=CC=1>FC(F)(F)C(O)=O.ClCCl>[CH3:10][O:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH:1]2[CH2:23][CH2:13][N:14]([CH2:15][CH:16]=[CH2:17])[CH2:2]2)[N:4]=1

Participants

5

Reactant 3

HCID 7501StyreneHCID 18374742N-(methoxymethyl)-N-((trimethylsilyl)methyl)prop-2-en-1-amineHCID 190915662-Methoxy-6-vinylpyridine

Product 1

HCID 895004922-(1-Allylpyrrolidin-3-yl)-6-methoxypyridineYield 30%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

To a solution of 2-ethenyl-6-methoxypyridine a1-51 (400 mg, 3 mmol, 1 eq) in trifluoroacetic acid/dichloromethane (200 μl/2 ml) is added N-(methoxymethyl)-N-[(trimethylsilyl)methyl]prop-2-en-1-amine until all styrene a1-51 is consumed. The solvent is removed under vacuum and the crude residue is purified by basic reverse phase chromatography over silicagel (gradient: CH3CN/H2O/NH4OH from 50/50/0.1 to 80/20/0.1) to afford 210 mg of pure 2-methoxy-6-[1-(prop-2-en-1-yl)pyrrolidin-3-yl]pyridine a1-55.

Workup

  1. customis consumed
  2. customThe solvent is removed under vacuum
  3. customthe crude residue is purified by basic reverse phase chromatography over silicagel (gradient: CH3CN/H2O/NH4OH from 50/50/0.1 to 80/20/0.1)

Sources & evidence

ORD record
ord-4df6ae0a57994fd588ba959c84ffc9ed
Source dataset
uspto-grants-2015_06
Patent number
US09067930B2

Reaction notes

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