(S)-1-(pyrrolidin-2-ylmethyl)piperidine → 2-Fluoro-5-[(E)-3-oxo-3-((S)-2-((piperidin-1-yl)methyl)pyrrolidin-1-yl)propenyl]benzonitrile
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5](/[CH:10]=[CH:11]/[C:12]([OH:14])=O)[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].[NH:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[CH2:20][N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>>[F:9][C:8]1[CH:7]=[CH:6][C:5](/[CH:10]=[CH:11]/[C:12](=[O:14])[N:15]2[CH2:19][CH2:18][CH2:17][C@H:16]2[CH2:20][N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:4][C:3]=1[C:1]#[N:2]Participants
3
Procedure
300 mg of the title compound were synthesized as described for (E)-3-(4-bromophenyl)-1-((S)-2-((pyrrolidin-1-yl)methyl)pyrrolidin-1-yl)propenone, using (E)-3-(3-cyano-4-fluorophenyl)acrylic acid instead of (E)-4-bromocinnamic acid and 1-(((S)-pyrrolidin-2-yl)methyl)piperidine instead of (S)-2-((pyrrolidin-1-yl)methyl)pyrrolidine.
Sources & evidence
- ORD record
- ord-08ea66be3fe840bdbb926b435fec1b9c
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07101898B2
Reaction notes
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