6-(Bromomethyl)-1-methylquinolin-2(1H)-one → (2S,4R)-4-[3-(1,2-dihydro-1-methyl-2-oxoquinolin-6-ylmethoxy)phenyl]-4-methoxy-2-methyltetrahydropyran

HRID 1609520Notes

Reaction equation

HRID 1609520 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][C:16]1[CH:17]=[C:18]([C@@:22]2([O:29][CH3:30])[CH2:27][CH2:26][O:25][C@@H:24]([CH3:28])[CH2:23]2)[CH:19]=[CH:20][CH:21]=1>>[CH3:13][N:9]1[C:10]2[C:5](=[CH:4][C:3]([CH2:2][O:15][C:16]3[CH:17]=[C:18]([C@@:22]4([O:29][CH3:30])[CH2:27][CH2:26][O:25][C@@H:24]([CH3:28])[CH2:23]4)[CH:19]=[CH:20][CH:21]=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 22845133(2S,4R)-4-(3-hydroxyphenyl)-4-methoxy-2-methyltetrahydropyran

Product 1

HCID 67796314(2S,4R)-4-[3-(1,2-dihydro-1-methyl-2-oxoquinolin-6-ylmethoxy)phenyl]-4-methoxy-2-methyltetrahydropyranYield 69%

Procedure

Using the procedure described in Example 1, 6-bromomethyl-1,2-dihydro-1-methylquinolin-2-one was reacted with (2S,4R)-4-(3-hydroxyphenyl)-4-methoxy-2-methyltetrahydropyran to give (2S,4R)-4-[3-(1,2-dihydro-1-methyl-2-oxoquinolin-6-ylmethoxy)phenyl]-4-methoxy-2-methyltetrahydropyran in 69% yield, m.p. 88°-90° C.

Sources & evidence

ORD record
ord-014fae7718e148c795dc28ce0de5f847
Source dataset
uspto-grants-1995_03
Patent number
US05401751

Reaction notes

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