1-Piperonylpiperazine → (3Ez,5s)-5-{[4-(1,3-benzodioxol-5-ylmethyl)-1-piperazinyl]carbonyl}-1-[(2-oxo-6-pentyl-2h-pyran-3-yl)carbonyl]-3-pyrrolidinone o-(tert-butyl)oxime

HRID 1349189Notes

Reaction equation

HRID 1349189 reaction equation
C(O[C:6]([N:8]1[CH2:12][C:11](=[N:13][O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:10][C@H:9]1[C:19]([OH:21])=O)=[O:7])(C)(C)C.[O:22]=[C:23]1[C:28](C(Cl)=O)=[CH:27][CH:26]=[C:25]([CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[O:24]1.[O:37]1[C:41]2[CH:42]=[CH:43][C:44]([CH2:46][N:47]3[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]3)=[CH:45][C:40]=2[O:39][CH2:38]1>>[C:15]([O:14][N:13]=[C:11]1[CH2:10][C@@H:9]([C:19]([N:50]2[CH2:51][CH2:52][N:47]([CH2:46][C:44]3[CH:43]=[CH:42][C:41]4[O:37][CH2:38][O:39][C:40]=4[CH:45]=3)[CH2:48][CH2:49]2)=[O:21])[N:8]([C:6]([C:28]2[C:23](=[O:22])[O:24][C:25]([CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[CH:26][CH:27]=2)=[O:7])[CH2:12]1)([CH3:16])([CH3:17])[CH3:18]

Participants

4

Reactant 3

HCID 944261-PiperonylpiperazineHCID 222235122-oxo-6-pentyl-2H-pyran-3-carbonyl chlorideHCID 131725425(2S,4EZ)-1-(tertbutoxycarbonyl)-4-(tert-butoxyimino)-2-pyrrolidinecarboxylic acid

Product 1

HCID 131725542(3Ez,5s)-5-{[4-(1,3-benzodioxol-5-ylmethyl)-1-piperazinyl]carbonyl}-1-[(2-oxo-6-pentyl-2h-pyran-3-yl)carbonyl]-3-pyrrolidinone o-(tert-butyl)oxime

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-1-(tert-butoxycarbonyl)-4-(tert-butoxyimino)-2-pyrrolidinecarboxylic acid, 2-oxo-6-pentyl-2H-pyran-3-carbonyl chloride, and 1-(1,3-benzodioxol-5-ylmethyl)piperazine the title compound was obtained in 59% purity by LC/MS. MS(ESI+): m/z=595.4.

Sources & evidence

ORD record
ord-2ebc34db4e1e4e5ba9db282be9061026
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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