6-Mercapto-3,4-dihydroquinolin-2(1H)-one → (2S,4R)-4-hydroxy-2-methyl-4-[3-(2-oxo-1,2,3,4-tetrahydroquinolin-6-ylthio)phenyl]tetrahydropyran

HRID 2260610Notes

Reaction equation

HRID 2260610 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.[OH:13][C@:14]1([C:21]2[CH:26]=[CH:25][CH:24]=[C:23](I)[CH:22]=2)[CH2:19][CH2:18][O:17][C@@H:16]([CH3:20])[CH2:15]1>>[OH:13][C@:14]1([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([S:1][C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]4)[CH:22]=2)[CH2:19][CH2:18][O:17][C@@H:16]([CH3:20])[CH2:15]1

Participants

3

Reactant 2

HCID 131098326-Mercapto-3,4-dihydroquinolin-2(1H)-oneHCID 54517626(2S,4R)-4-hydroxy-4-(3-iodophenyl)-2-methyltetrahydropyran

Product 1

HCID 57063103(2S,4R)-4-hydroxy-2-methyl-4-[3-(2-oxo-1,2,3,4-tetrahydroquinolin-6-ylthio)phenyl]tetrahydropyranYield 25%

Procedure

Using an analogous procedure to that described in Example 6, 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-hydroxy-2-methyl-4-[3-(2-oxo-1,2,3,4-tetrahydroquinolin-6-ylthio)phenyl]tetrahydropyran in 25% yield, m.p. 180°-181° C. (recrystallised from ethyl acetate);

Sources & evidence

ORD record
ord-4960ccc1a7d646f495b42b6451f811b8
Source dataset
uspto-grants-1995_12
Patent number
US05478842

Reaction notes

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