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

HRID 490600Notes

Reaction equation

HRID 490600 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.[C:33]1([N:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[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:42]1[CH2:43][CH2:44][N:39]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:40][CH2:41]1)=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 70961-PhenylpiperazineHCID 675474701-Benzyl-4-[tert-butoxycarbonyl-(2,4-difluoro-benzyl)-amino]-pyrrolidine-2-carboxylic acid

Product 1

HCID 25121017[(2S,4S)-1-Benzyl-4-(2,4-difluoro-benzylamino)-pyrrolidin-2-yl]-(4-phenyl-piperazin-1-yl)-methanoneYield 9.5%

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-phenyl-piperazine instead of 2-piperazin-1-yl-benzonitrile, to the title compound (6.3 mg, 9.5%) as light yellow oil. MS m/e=491.4 [M+H]+.

Sources & evidence

ORD record
ord-8d2b5fbcc6674c668a2d32746e390e99
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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