2-Pyrrolidinone, 4-hydroxy-, (4S)- → (S)-1-{4-[4-(2,4-dimethylphenyl)piperazine-1-carbonyl]phenyl}-4-hydroxypyrrolidin-2-one

HRID 2411730Notes

Reaction equation

HRID 2411730 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=3[CH3:23])[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[OH:24][C@@H:25]1[CH2:29][NH:28][C:27](=[O:30])[CH2:26]1>>[CH3:23][C:17]1[CH:18]=[C:19]([CH3:22])[CH:20]=[CH:21][C:16]=1[N:13]1[CH2:14][CH2:15][N:10]([C:8]([C:5]2[CH:6]=[CH:7][C:2]([N:28]3[CH2:29][C@@H:25]([OH:24])[CH2:26][C:27]3=[O:30])=[CH:3][CH:4]=2)=[O:9])[CH2:11][CH2:12]1

Participants

3

Reactant 2

HCID 1550842-Pyrrolidinone, 4-hydroxy-, (4S)-HCID 58484623(4-Bromophenyl)[4-(2,4-dimethylphenyl)piperazin-1-yl]methanone

Product 1

HCID 71252641(S)-1-{4-[4-(2,4-dimethylphenyl)piperazine-1-carbonyl]phenyl}-4-hydroxypyrrolidin-2-oneYield 38.6%

Procedure

Using (4-bromophenyl) [4-(2,4-dimethylphenyl)piperazin-1-yl]methanone (1.87 g) described in Preparation Example 170 and (S)-4-hydroxypyrrolidin-2-one (556 mg) and by the reaction and treatment in the same manner as in Example 1, the title compound (760 mg) was obtained.

Sources & evidence

ORD record
ord-d1d0c736e0464e6bb4cd221f5829f2b9
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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