N-methyl-2,5-di(trimethyl silyl) pyrrolidine → (1R,2R,4S)-2-(6-Chloropyridin-3-yl)-7-methyl-7-azabicyclo[2.2.1]heptane

HRID 1721447Notes

Reaction equation

HRID 1721447 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[CH2:9])=[CH:4][CH:3]=1.[CH3:10][N:11]1[CH:15]([Si](C)(C)C)[CH2:14][CH2:13][CH:12]1[Si](C)(C)C>C(#N)C>[CH3:10][N:11]1[CH:15]2[CH:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[N:7][CH:6]=3)[CH2:9][CH:12]1[CH2:13][CH2:14]2

Participants

4

Reactant 2

HCID 10966292N-methyl-2,5-di(trimethyl silyl) pyrrolidineHCID 118154432-Chloro-5-vinyl-pyridine

Product 1

HCID 11601009(1R,2R,4S)-2-(6-Chloropyridin-3-yl)-7-methyl-7-azabicyclo[2.2.1]heptaneYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a acetonitrile solution containing 3 gms of Ag(1)F. 1.2 gms of dipolarophile (6-chloro-3-vinyl pyridine) was added to 2 gms of N-methyl-2,5-di(trimethyl silyl) pyrrolidine at 25° C. After stirring the reaction mixture for 2 to 2.5 hours, the reaction mixture was filtered through a plug of celite. The solvent was evaporated to give N-methyl Epibatidine in 80% yield which was further purified by column chromatography. Hydrogenation of N-methyl Epibatidine with pd/c for 22 hours gave 70% yield of Epibatidine.

Workup

  1. filtrationthe reaction mixture was filtered through a plug of celite
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-5b73969f822246c48ade8a71976d69f9
Source dataset
uspto-grants-1996_04
Patent number
US05510490

Reaction notes

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