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

HRID 490596Notes

Reaction equation

HRID 490596 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.[CH:33]([N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1)([CH3:35])[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:39]1[CH2:40][CH2:41][N:36]([CH:33]([CH3:35])[CH3:34])[CH2:37][CH2:38]1)=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 780131-IsopropylpiperazineHCID 675474701-Benzyl-4-[tert-butoxycarbonyl-(2,4-difluoro-benzyl)-amino]-pyrrolidine-2-carboxylic acid

Product 1

HCID 68861114[(2S,4S)-1-Benzyl-4-(2,4-difluoro-benzylamino)-pyrrolidin-2-yl]-(4-isopropyl-piperazin-1-yl)-methanoneYield 9.3%

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-isopropyl-piperazine instead of 2-piperazin-1-yl-benzonitrile, to the title compound (6.2 mg, 9.3%) as light yellow oil. MS m/e=457.4 [M+H]+.

Sources & evidence

ORD record
ord-43c93d4d63474a12ac4a2b0b8396366b
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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