Diethyl Oxalate → Ethyl 4-Methoxyatropate

HRID 1859352Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1)[CH3:2].[CH2:15](OC(=O)C(OCC)=O)C.[H-].[Na+]>>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([C:5](=[CH2:15])[C:4]([O:3][CH2:1][CH3:2])=[O:14])=[CH:7][CH:8]=1

Participants

Reactant 3

HCID 7268Diethyl Oxalate

HCID 24758Sodium hydride

HCID 84174Ethyl 4-methoxyphenylacetate

Product 1

HCID 11275761Ethyl 4-Methoxyatropate

Procedure

A process for preparing a compound of formula (6): ##STR120## characterized in that a compound of formula (1): ##STR121## is reacted with oxalic acid diethyl ester and sodium hydride to produce a compound of formula (2): ##STR122## the resulting compound of formula (2) is reacted with 3-methoxybenzenethiol represented by the formula: ##STR123## to produce a compound of formula (3): ##STR124## the resulting compound of formula (3) is reacted with hydrochloric acid to produce a compound of formula (4): ##STR125## the compound of formula formula (4) is then cyclized to produce a compound of formula (5): ##STR126## and the compound of formula (5) is reacted with methyl iodide in the presence of lithium diisopropylamide to produce the compound of formula (6).

Sources & evidence

ORD record: ord-243435d8352e47fd93c36697a9a18c9f
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06153768

Reaction notes

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