Tetrahydrofuran → racemic (2'R,3R,4'S)-6-chloro-4'-(3-chlorophenyl)-2'-(3-ethynyl-phenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 2151596Notes

Reaction equation

HRID 2151596 reaction equation
[CH3:32][Si:33]([CH3:34])([CH3:35])[C:36]#[CH:37].[CH3:38][CH2:39][N:40]([CH2:41][CH3:42])[CH2:43][CH3:44].[Cl:1][c:2]1[cH:3][cH:4][c:5]2[c:9]([cH:10]1)[NH:8][C:7](=[O:11])[C:6]21[CH:12]([c:25]2[cH:26][c:27]([I:31])[cH:28][cH:29][cH:30]2)[NH:13][C:14](=[O:24])[CH2:15][CH:16]1[c:17]1[cH:18][c:19]([Cl:23])[cH:20][cH:21][cH:22]1.[Cu:50][I:51].[O:45]1[CH2:46][CH2:47][CH2:48][CH2:49]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5]2[c:9]([cH:10]1)[NH:8][C:7](=[O:11])[C:6]21[CH:12]([c:25]2[cH:26][c:27]([C:36]#[CH:37])[cH:28][cH:29][cH:30]2)[NH:13][C:14](=[O:24])[CH2:15][CH:16]1[c:17]1[cH:18][c:19]([Cl:23])[cH:20][cH:21][cH:22]1

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 66111TrimethylsilylacetyleneHCID 76568101racemic (2'R,3R,4'S)-6-chloro-4'-(3-chlorophenyl)-2'-(3-iodophenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

Product 1

HCID 76567966racemic (2'R,3R,4'S)-6-chloro-4'-(3-chlorophenyl)-2'-(3-ethynyl-phenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

Sources & evidence

ORD record
ord-7d0537e9eedb44598f95b9b08a894bc3
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (4/10)

Reaction notes

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