1-(2-Methoxyethyl)piperazine → [(2s,4s)-1-Benzyl-4-(2,4-difluoro-benzylamino)-pyrrolidin-2-yl]-[4-(2-methoxy-ethyl)-piperazin-1-yl]-methanone

HRID 490595Notes

Reaction equation

HRID 490595 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.[CH3:33][O:34][CH2:35][CH2:36][N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]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:40]1[CH2:41][CH2:42][N:37]([CH2:36][CH2:35][O:34][CH3:33])[CH2:38][CH2:39]1)=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 27346381-(2-Methoxyethyl)piperazineHCID 675474701-Benzyl-4-[tert-butoxycarbonyl-(2,4-difluoro-benzyl)-amino]-pyrrolidine-2-carboxylic acid

Product 1

HCID 67549396[(2s,4s)-1-Benzyl-4-(2,4-difluoro-benzylamino)-pyrrolidin-2-yl]-[4-(2-methoxy-ethyl)-piperazin-1-yl]-methanoneYield 8.9%

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-(2-methyoxy-ethyl)-piperazine instead of 2-piperazin-1-yl-benzonitrile, to the title compound (5.7 mg, 8.9%) as light yellow oil. MS m/e=473.4 [M+H]+.

Sources & evidence

ORD record
ord-30368b5e50684c5381760d51cc8cbf5e
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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