Methyl iodide → (3RS,4SR)-4-[3-(1,2-dihydro-1-methyl-2-oxoquinolin-6-ylmethoxy)phenyl]-3,4-dimethoxytetrahydropyran

HRID 654819Notes

Reaction equation

HRID 654819 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][O:13][C:14]3[CH:15]=[C:16]([C:20]4([O:27][CH3:28])[CH2:25][CH2:24][O:23][CH2:22][CH:21]4[OH:26])[CH:17]=[CH:18][CH:19]=3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]1=[O:29].CI.[CH2:32]1OCCOCCOCCOCCOC1>>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][O:13][C:14]3[CH:15]=[C:16]([C:20]4([O:27][CH3:28])[CH2:25][CH2:24][O:23][CH2:22][CH:21]4[O:26][CH3:32])[CH:17]=[CH:18][CH:19]=3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]1=[O:29]

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 3633615-Crown-5HCID 67796585(3RS,4SR)-4-[3-(1,2-dihydro-1-methyl-2-oxoquinolin-6-ylmethoxy)phenyl]-3-hydroxy-4-methoxytetrahydropyran

Product 1

HCID 67795507(3RS,4SR)-4-[3-(1,2-dihydro-1-methyl-2-oxoquinolin-6-ylmethoxy)phenyl]-3,4-dimethoxytetrahydropyranYield 78%

Procedure

Using the methylation procedure described in the portion of Example 1 which is concerned with the preparation of starting materials, (3RS,4SR)-4-[3-(1,2-dihydro-1-methyl-2-oxoquinolin-6-ylmethoxy)phenyl]-3-hydroxy-4-methoxytetrahydropyran was reacted with methyl iodide in the presence of 15-crown-5 to give (3RS,4SR)-4-[3-(1,2-dihydro-1-methyl-2-oxoquinolin-6-ylmethoxy)phenyl]-3,4-dimethoxytetrahydropyran in 78% yield, as a glass.

Sources & evidence

ORD record
ord-b8c051c7fd0a4ab689e8212f2c335396
Source dataset
uspto-grants-1992_07
Patent number
US05134148

Reaction notes

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