(S)-5-(Hydroxymethyl)-2-pyrrolidinone → (S)-1-{4-[4-(2,4-dimethylphenyl)piperazine-1-carbonyl]phenyl}-5-hydroxymethylpyrrolidin-2-one

HRID 2411713Notes

Reaction equation

HRID 2411713 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][CH2:25][C@H:26]1[NH:30][C:29](=[O:31])[CH2:28][CH2:27]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:30]3[C@H:26]([CH2:25][OH:24])[CH2:27][CH2:28][C:29]3=[O:31])=[CH:3][CH:4]=2)=[O:9])[CH2:11][CH2:12]1

Participants

3

Reactant 2

HCID 643511(S)-5-(Hydroxymethyl)-2-pyrrolidinoneHCID 58484623(4-Bromophenyl)[4-(2,4-dimethylphenyl)piperazin-1-yl]methanone

Product 1

HCID 71252249(S)-1-{4-[4-(2,4-dimethylphenyl)piperazine-1-carbonyl]phenyl}-5-hydroxymethylpyrrolidin-2-oneYield 50.8%

Procedure

Using (4-bromophenyl)[4-(2,4-dimethylphenyl)piperazin-1-yl]methanone (1.87 g) described in Preparation Example 170 and (S)-5-hydroxymethylpyrrolidin-2-one (556 mg) and by the reaction and treatment in the same manner as in Example 1, the title compound (1.00 g) was obtained.

Sources & evidence

ORD record
ord-cc597919f7d840b6958067e13560fc50
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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