6-(Bromomethyl)-1-methylquinolin-2(1H)-one → (3RS,4SR)-4-[3-(1,2-dihydro-1-methyl-2-oxoquinolin-6-ylmethoxy)phenyl]-3-hydroxy-4-methoxytetrahydropyran

HRID 654818Notes

Reaction equation

HRID 654818 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:13])[C:8](=[O:14])[CH:7]=[CH:6]2.[OH:15][CH:16]1[C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([OH:30])[CH:25]=2)([O:22][CH3:23])[CH2:20][CH2:19][O:18][CH2:17]1>>[CH3:13][N:9]1[C:10]2[C:5](=[CH:4][C:3]([CH2:2][O:30][C:26]3[CH:25]=[C:24]([C:21]4([O:22][CH3:23])[CH2:20][CH2:19][O:18][CH2:17][CH:16]4[OH:15])[CH:29]=[CH:28][CH:27]=3)=[CH:12][CH:11]=2)[CH:6]=[CH:7][C:8]1=[O:14]

Participants

3

Reactant 2

HCID 151990656-(Bromomethyl)-1-methylquinolin-2(1H)-oneHCID 67796247(3RS,4SR)-3-hydroxy-4-(3-hydroxyphenyl)-4-methoxytetrahydropyran

Product 1

HCID 67796585(3RS,4SR)-4-[3-(1,2-dihydro-1-methyl-2-oxoquinolin-6-ylmethoxy)phenyl]-3-hydroxy-4-methoxytetrahydropyranYield 84%

Procedure

Using the procedure described in Example 1, 6-bromomethyl-1,2-dihydro-1-methylquinolin-2-one was reacted with (3RS,4SR)-3-hydroxy-4-(3-hydroxyphenyl)-4-methoxytetrahydropyran to give (3RS,4SR)-4-[3-(1,2-dihydro-1-methyl-2-oxoquinolin-6-ylmethoxy)phenyl]-3-hydroxy-4-methoxytetrahydropyran in 84% yield, m.p. 62°-66° C.

Sources & evidence

ORD record
ord-2593f6a46920499bb88f31f8b763459d
Source dataset
uspto-grants-1992_07
Patent number
US05134148

Reaction notes

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