Ethyl 3-oxopyrrolidine-1-carboxylate → 1-Ethoxycarbonyl-3-{5-fluoro-3-[4-(2-methyl1,3-dioxolan-2-yl)phenylthio]phenyl}-3-hydroxypyrrolidine

HRID 37562Notes

Reaction equation

HRID 37562 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([CH3:21])[O:20][CH2:19][CH2:18][O:17]3)=[CH:12][CH:11]=2)[CH:5]=[C:6](Br)[CH:7]=1.[CH2:22]([O:24][C:25]([N:27]1[CH2:31][CH2:30][C:29](=[O:32])[CH2:28]1)=[O:26])[CH3:23]>>[CH2:22]([O:24][C:25]([N:27]1[CH2:31][CH2:30][C:29]([C:6]2[CH:7]=[C:2]([F:1])[CH:3]=[C:4]([S:9][C:10]3[CH:15]=[CH:14][C:13]([C:16]4([CH3:21])[O:20][CH2:19][CH2:18][O:17]4)=[CH:12][CH:11]=3)[CH:5]=2)([OH:32])[CH2:28]1)=[O:26])[CH3:23]

Participants

3

Reactant 2

HCID 277754Ethyl 3-oxopyrrolidine-1-carboxylateHCID 199358785-Fluoro-3-[4-(2-methyl-1,3-dioxolan-2-yl)phenylthio]bromobenzene

Product 1

HCID 199358391-Ethoxycarbonyl-3-{5-fluoro-3-[4-(2-methyl1,3-dioxolan-2-yl)phenylthio]phenyl}-3-hydroxypyrrolidineYield 50%

Procedure

Using an analogous procedure to that described in the fourth paragraph of the portion of Example 28 which is concerned with the preparation of starting materials, 5-fluoro-3-[4-(2-methyl-1,3-dioxolan-2-yl)phenylthio]bromobenzene was reacted with 1-ethoxycarbonylpyrrolidin-3-one to give 1-ethoxycarbonyl-3-{5-fluoro-3-[4-(2-methyl1,3-dioxolan-2-yl)phenylthio]phenyl}-3-hydroxypyrrolidine as a gum in 50% yield.

Sources & evidence

ORD record
ord-8b71f0028fff4b4bb96b8fcd4a9c2f1d
Source dataset
uspto-grants-1995_05
Patent number
US05420298

Reaction notes

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