(S)-1-(pyrrolidin-2-ylmethyl)piperidine → (E)-1-((S)-2-((Piperidin-1-yl)methyl)pyrrolidin-1-yl)-3-(4-(trifluoromethyl)phenyl)but-2-en-1-one

HRID 2212053Notes

Reaction equation

HRID 2212053 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][C:6](/[C:9](/[CH3:14])=[CH:10]/[C:11]([OH:13])=O)=[CH:5][CH:4]=1.[NH:17]1[CH2:21][CH2:20][CH2:19][C@H:18]1[CH2:22][N:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>>[N:23]1([CH2:22][C@@H:18]2[CH2:19][CH2:20][CH2:21][N:17]2[C:11](=[O:13])/[CH:10]=[C:9](/[C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:16])[F:15])=[CH:8][CH:7]=2)\[CH3:14])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

3

Reactant 2

HCID 7022796(S)-1-(pyrrolidin-2-ylmethyl)piperidineHCID 287914333-[4-(Trifluoromethyl)phenyl]but-2-enoic acid

Product 1

HCID 58697228(E)-1-((S)-2-((Piperidin-1-yl)methyl)pyrrolidin-1-yl)-3-(4-(trifluoromethyl)phenyl)but-2-en-1-one

Procedure

110 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-(4-(trifluoromethyl)phenyl)but-2-enoic 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-d74bc8e608494e52996d6b13adbfd327
Source dataset
uspto-grants-2006_09
Patent number
US07101898B2

Reaction notes

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