2-Methylpyrrolidine → 1-[2-(6-Bromo-naphthalen-2-yl)-ethyl]-2-methyl-pyrrolidine
Reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:12]=[CH2:13])[CH:8]=2)[CH:3]=1.[CH3:14][CH:15]1[CH2:19][CH2:18][CH2:17][NH:16]1.C([Li])CCC>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH2:12][CH2:13][N:16]1[CH2:17][CH2:18][CH2:19][CH:15]1[CH3:14])[CH:6]=[CH:5]2Participants
Procedure
2-Bromo-6-vinyl-naphthalene is treated with a 2-methylpyrrolidine anion generated with n-butyllithium to provide 1-[2-(6-bromo-naphthalen-2-yl)-ethyl]-2-methyl-pyrrolidine. Preferably, about 1.2 to about 2.5 molar equivalents of 2-methylpyrrolidine are used for the reaction. The reaction typically is accomplished in an organic solvent, for example, THF, methyl-t-butyl ether (MTBE), Et2O, and DME. The preferred solvent is tetrahydrofuran (THF). The n-butyllithium is added to a THF solution of 2-methylpyrrolidine in a controlled fashion, typically in a dropwise manner. To this solution is added a THF solution of 2-bromo-6-vinyl-naphthalene. Alternatively, it is also suitable to the THF solution of 2-bromo-6-vinyl-naphthalene to the solution of 2-methylpyrrolidine and n-butyllithium. The reaction is accomplished at below room temperature, typically in a temperature range from about 0° C. to about −20° C. From about 0.3 to about 0.7 molar equivalents of n-butyllithium are used relative to the 2-bromo-6-vinylnaphthalene compound. The resulting compound is 1-[2-(6-bromo-naphthalen-2-yl)-ethyl]-2-methyl-pyrrolidine.
Sources & evidence
- ORD record
- ord-e083aa84c0594c45877ba93a85803020
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07145005B2
Reaction notes
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