Ethanol → 4-{4-[2-(2,4-bis-benzyloxy-5-isopropenyl-benzoyl)-2,3-dihydro-1H-isoindol-5-yl]phenyl}piperazine-1-carboxylic acid tert-butyl ester

HRID 812279Notes

Reaction equation

HRID 812279 reaction equation
[C:38]([CH3:39])([CH3:40])([CH3:41])[O:42][C:43](=[O:44])[N:45]1[CH2:46][CH2:47][N:48]([c:51]2[cH:52][cH:53][c:54]([B:57]3[O:58][C:59]([CH3:60])([CH3:61])[C:62]([CH3:63])([CH3:64])[O:65]3)[cH:55][cH:56]2)[CH2:49][CH2:50]1.[C:66](=[O:67])([O-:68])[O-:69].[CH2:1]([c:2]1[cH:3][cH:4][cH:5][cH:6][cH:7]1)[O:8][c:9]1[c:10]([C:26](=[O:27])[N:28]2[CH2:29][c:30]3[cH:31][cH:32][c:33]([Br:37])[cH:34][c:35]3[CH2:36]2)[cH:11][c:12]([C:23](=[CH2:24])[CH3:25])[c:13]([O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:14]1.[CH2:72]([OH:73])[CH3:74].[CH3:83][CH2:84][O:85][C:86]([CH3:87])=[O:88].[K+:70].[K+:71].[OH2:75].[c:76]1([CH3:77])[cH:78][cH:79][cH:80][cH:81][cH:82]1>>[CH2:1]([c:2]1[cH:3][cH:4][cH:5][cH:6][cH:7]1)[O:8][c:9]1[c:10]([C:26](=[O:27])[N:28]2[CH2:29][c:30]3[cH:31][cH:32][c:33](-[c:54]4[cH:53][cH:52][c:51]([N:48]5[CH2:47][CH2:46][N:45]([C:43]([O:42][C:38]([CH3:39])([CH3:40])[CH3:41])=[O:44])[CH2:50][CH2:49]5)[cH:56][cH:55]4)[cH:34][c:35]3[CH2:36]2)[cH:11][c:12]([C:23](=[CH2:24])[CH3:25])[c:13]([O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:14]1

Participants

9

Reactant 8

HCID 702EthanolHCID 813Potassium Cation2×HCID 962WaterHCID 1140TolueneHCID 8857Ethyl AcetateHCID 19660Carbonate IonHCID 27955144-(4-tert-Butoxycarbonylpiperazinyl)phenylboronic acid, pinacol esterHCID 46915776(2,4-Bis-benzyloxy-5-isopropenyl-phenyl)-(5-bromo-1,3-dihydro-isoindol-2-yl)-methanone

Product 1

HCID 666725624-{4-[2-(2,4-bis-benzyloxy-5-isopropenyl-benzoyl)-2,3-dihydro-1H-isoindol-5-yl]phenyl}piperazine-1-carboxylic acid tert-butyl ester

Sources & evidence

ORD record
ord-ffcf4b8c37ce48008e81fe40a305e0b9
Source dataset
Test data from https://doi.org/10.1039/C8SC04228D

Reaction notes

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