8-Chloro-6-mercapto-1,2,3,4-tetrahydroquinolin-2-one → (2S,4R)-4-[3-(8-chloro-2-oxo-1,2,3,4-tetrahydroquinolin-6-ylthio)phenyl]-4-hydroxy-2-methyltetrahydropyran

HRID 2260612Notes

Reaction equation

HRID 2260612 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([SH:13])[CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2.[OH:14][C@:15]1([C:22]2[CH:27]=[CH:26][CH:25]=[C:24](I)[CH:23]=2)[CH2:20][CH2:19][O:18][C@@H:17]([CH3:21])[CH2:16]1>>[Cl:1][C:2]1[CH:3]=[C:4]([S:13][C:26]2[CH:27]=[C:22]([C@@:15]3([OH:14])[CH2:20][CH2:19][O:18][C@@H:17]([CH3:21])[CH2:16]3)[CH:23]=[CH:24][CH:25]=2)[CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2

Participants

3

Reactant 2

HCID 224138108-Chloro-6-mercapto-1,2,3,4-tetrahydroquinolin-2-oneHCID 54517626(2S,4R)-4-hydroxy-4-(3-iodophenyl)-2-methyltetrahydropyran

Product 1

HCID 54213124(2S,4R)-4-[3-(8-chloro-2-oxo-1,2,3,4-tetrahydroquinolin-6-ylthio)phenyl]-4-hydroxy-2-methyltetrahydropyranYield 69%

Procedure

Using an analogous procedure to that described in Example 6, 8-chloro-6-mercapto-1,2,3,4-tetrahydroquinolin-2-one was reacted with (2S,4R)-4-hydroxy-4-(3-iodophenyl)-2-methyltetrahydropyran to give (2S,4R)-4-[3-(8-chloro-2-oxo-1,2,3,4-tetrahydroquinolin-6-ylthio)phenyl]-4-hydroxy-2-methyltetrahydropyran in 69% yield as a gum;

Sources & evidence

ORD record
ord-c14d46a807c149939201bbdadd1c7013
Source dataset
uspto-grants-1995_12
Patent number
US05478842

Reaction notes

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