Water → rac-(2'S,3'S,4'S)-4'-[4-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-butyl]-6-chloro-2'-(3-chloro-2-fluoro-phenyl)-1H-spiro[indole-3,3'-pyrrolidin]-2-one

HRID 665143Notes

Reaction equation

HRID 665143 reaction equation
[CH3:51][c:52]1[cH:53][cH:54][cH:55][cH:56][cH:57]1.[Cl:29][c:30]1[c:31]([F:38])[c:32]([CH:33]=[O:34])[cH:35][cH:36][cH:37]1.[NH2:1][CH2:2][CH:3]([CH2:4][C:5]([CH2:6][CH2:7][O:8][Si:9]([CH3:10])([CH3:11])[C:12]([CH3:13])([CH3:14])[CH3:15])([CH3:16])[CH3:17])[CH:18]1[C:19](=[O:28])[NH:20][c:21]2[cH:22][c:23]([Cl:27])[cH:24][cH:25][c:26]21.[OH2:39].[c:40]1([CH3:41])[cH:42][cH:43][c:44]([S:45]([OH:46])(=[O:47])=[O:48])[cH:49][cH:50]1>>[NH:1]1[CH2:2][CH:3]([CH2:4][C:5]([CH2:6][CH2:7][O:8][Si:9]([CH3:10])([CH3:11])[C:12]([CH3:13])([CH3:14])[CH3:15])([CH3:16])[CH3:17])[C:18]2([C:19](=[O:28])[NH:20][c:21]3[cH:22][c:23]([Cl:27])[cH:24][cH:25][c:26]32)[CH:33]1[c:32]1[c:31]([F:38])[c:30]([Cl:29])[cH:37][cH:36][cH:35]1

Participants

6

Reactant 5

HCID 962WaterHCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 7363353-Chloro-2-fluorobenzaldehydeHCID 58398996Racemic 3-[1-aminomethyl-5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-pentyl]-6-chloro-1,3-dihydro-indol-2-one

Product 1

HCID 67336835rac-(2'S,3'S,4'S)-4'-[4-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-butyl]-6-chloro-2'-(3-chloro-2-fluoro-phenyl)-1H-spiro[indole-3,3'-pyrrolidin]-2-one

Sources & evidence

ORD record
ord-e331bc8377e546258cbce43c6697e4f9
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (3/10)

Reaction notes

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