1,2-Dichloroethane → (RS)-1-{(4-chlorophenyl)[4-(pyrrolidylmethyl)phenyl]methyl}-3-[(3,5-difluorophenyl)(methylsulfonyl)methylene]azetidine

HRID 136810Notes

Reaction equation

HRID 136810 reaction equation
[C:34]([O:35][BH-:36]([O:37][C:38](=[O:39])[CH3:40])[O:41][C:42](=[O:43])[CH3:44])(=[O:45])[CH3:46].[CH2:48]1[CH2:49][CH2:50][NH:51][CH2:52]1.[Cl:1][c:2]1[cH:3][cH:4][c:5]([CH:8]([N:9]2[CH2:10][C:11](=[C:13]([S:14](=[O:15])(=[O:16])[CH3:17])[c:18]3[cH:19][c:20]([F:25])[cH:21][c:22]([F:24])[cH:23]3)[CH2:12]2)[c:26]2[cH:27][cH:28][c:29]([CH:32]=[O:33])[cH:30][cH:31]2)[cH:6][cH:7]1.[Cl:55][CH2:56][CH2:57][Cl:58].[Na+:47].[Na+:54].[OH-:53]>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([CH:8]([N:9]2[CH2:10][C:11](=[C:13]([S:14](=[O:15])(=[O:16])[CH3:17])[c:18]3[cH:19][c:20]([F:25])[cH:21][c:22]([F:24])[cH:23]3)[CH2:12]2)[c:26]2[cH:27][cH:28][c:29]([CH2:32][N:51]3[CH2:50][CH2:49][CH2:48][CH2:52]3)[cH:30][cH:31]2)[cH:6][cH:7]1

Participants

7

Reactant 6

HCID 111,2-DichloroethaneHCID 923Sodium ion2×HCID 961HydroxideHCID 31268PyrrolidineHCID 2724942TriacetoxyborohydrideHCID 22506638(-)-1-[(4-Chlorophenyl)(4-formylphenyl)methyl]-3-[(3,5-difluorophenyl)(methylsulfonyl)methylene]azetidine

Product 1

HCID 10280566(RS)-1-{(4-chlorophenyl)[4-(pyrrolidylmethyl)phenyl]methyl}-3-[(3,5-difluorophenyl)(methylsulfonyl)methylene]azetidine

Sources & evidence

ORD record
ord-b28c93303631459da7bc7ed73bae54fa
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (9/10)

Reaction notes

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