7-Fluoro-6-mercapto-1-methyl-1,2,3,4-tetrahydroquinolin-2-one → (2S,4R)-4-[3-(7-fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-ylthio)phenyl]-4-hydroxy-2-methyltetrahydropyran

HRID 2260611Notes

Reaction equation

HRID 2260611 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:13])[N:9]2[CH3:12])=[CH:4][C:3]=1[SH:14].[OH:15][C@:16]1([C:23]2[CH:28]=[CH:27][CH:26]=[C:25](I)[CH:24]=2)[CH2:21][CH2:20][O:19][C@@H:18]([CH3:22])[CH2:17]1>>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:13])[N:9]2[CH3:12])=[CH:4][C:3]=1[S:14][C:27]1[CH:28]=[C:23]([C@@:16]2([OH:15])[CH2:21][CH2:20][O:19][C@@H:18]([CH3:22])[CH2:17]2)[CH:24]=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 224137547-Fluoro-6-mercapto-1-methyl-1,2,3,4-tetrahydroquinolin-2-oneHCID 54517626(2S,4R)-4-hydroxy-4-(3-iodophenyl)-2-methyltetrahydropyran

Product 1

HCID 53744906(2S,4R)-4-[3-(7-fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-ylthio)phenyl]-4-hydroxy-2-methyltetrahydropyranYield 55%

Procedure

Using an analogous procedure to that described in Example 6, 7-fluoro-6-mercapto-1-methyl-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-(7-fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-ylthio)phenyl]-4-hydroxy-2-methyltetrahydropyran in 55% yield, m.p. 90-92° C. (recrystallised from diethyl ether);

Sources & evidence

ORD record
ord-c89fcf4d310340fd85fecb13b6e760ad
Source dataset
uspto-grants-1995_12
Patent number
US05478842

Reaction notes

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