1-(4-Ethoxyphenyl)piperazine → [(2S,4S)-1-Benzyl-4-(2,4-difluoro-benzylamino)-pyrrolidin-2-yl]-[4-(4-ethoxy-phenyl)-piperazin-1-yl]-methanone

HRID 490615Notes

Reaction equation

HRID 490615 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([N:13](C(OC(C)(C)C)=O)[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[F:22])[CH2:10][CH:9]1[C:30](O)=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:33]([O:35][C:36]1[CH:41]=[CH:40][C:39]([N:42]2[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]2)=[CH:38][CH:37]=1)[CH3:34]>>[CH2:1]([N:8]1[CH2:12][C@@H:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[F:22])[CH2:10][C@H:9]1[C:30]([N:45]1[CH2:44][CH2:43][N:42]([C:39]2[CH:38]=[CH:37][C:36]([O:35][CH2:33][CH3:34])=[CH:41][CH:40]=2)[CH2:47][CH2:46]1)=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 2314791-(4-Ethoxyphenyl)piperazineHCID 675474701-Benzyl-4-[tert-butoxycarbonyl-(2,4-difluoro-benzyl)-amino]-pyrrolidine-2-carboxylic acid

Product 1

HCID 67546930[(2S,4S)-1-Benzyl-4-(2,4-difluoro-benzylamino)-pyrrolidin-2-yl]-[4-(4-ethoxy-phenyl)-piperazin-1-yl]-methanoneYield 2.4%

Procedure

As described for Example 1f, 1-benzyl-4-[tert-butoxycarbonyl-(2,4-difluoro-benzyl)-amino]-pyrrolidine-2-carboxylic acid (60.0 mg, 0.134 mmol) was converted, using 1-(4-ethoxy-phenyl)-piperazine instead of 2-piperazin-1-yl-benzonitrile, to the title compound (1.7 mg, 2.4%) as light yellow oil. MS m/e=535.5 [M+H]+.

Sources & evidence

ORD record
ord-aed8c099ca7b45c8bda6ba199b327275
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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