1-Ethyl-6-mercapto-3,4-dihydroquinolin-2(1H)-one → (2S,4R)-4-[3-(1-ethyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-ylthio)phenyl]-4-hydroxy-2-methyltetrahydropyran

HRID 2260609Notes

Reaction equation

HRID 2260609 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([SH:13])=[CH:10][CH:11]=2)[CH2:6][CH2:5][C:4]1=[O:14])[CH3:2].[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>>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([S:13][C:27]3[CH:28]=[C:23]([C@@:16]4([OH:15])[CH2:21][CH2:20][O:19][C@@H:18]([CH3:22])[CH2:17]4)[CH:24]=[CH:25][CH:26]=3)=[CH:10][CH:11]=2)[CH2:6][CH2:5][C:4]1=[O:14])[CH3:2]

Participants

3

Reactant 2

HCID 224138271-Ethyl-6-mercapto-3,4-dihydroquinolin-2(1H)-oneHCID 54517626(2S,4R)-4-hydroxy-4-(3-iodophenyl)-2-methyltetrahydropyran

Product 1

HCID 53842638(2S,4R)-4-[3-(1-ethyl-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, 1-ethyl-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-(1-ethyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-ylthio)phenyl]-4-hydroxy-2-methyltetrahydropyran in 55% yield, m.p. 148°-149° C. (recrystallised from diethyl ether);

Sources & evidence

ORD record
ord-434d494ef2f6472f870367f1865bd5e0
Source dataset
uspto-grants-1995_12
Patent number
US05478842

Reaction notes

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