ChemicalBook CAS DataBase List 2-(2-carboxyethyl)-1-[(3,4-dimethoxyphenyl)methyl]-,1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-isoquinolinium benzenesulfonate

2-(2-carboxyethyl)-1-[(3,4-dimethoxyphenyl)methyl]-,1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-isoquinolinium benzenesulfonate synthesis

4synthesis methods

Product Name:2-(2-carboxyethyl)-1-[(3,4-dimethoxyphenyl)methyl]-,1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-isoquinolinium benzenesulfonate
CAS Number:1075727-06-8
Molecular formula:C30H37NO9S
Molecular Weight:587.68

1075727-00-2 Synthesis

(1R,2R)-1-[(3,4-Dimethoxyphenyl)methyl]-2-[3-(tert-butoxy)-3-oxopropyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinolinium benzenesulfonate

1075727-00-2
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2-(2-carboxyethyl)-1-[(3,4-dimethoxyphenyl)methyl]-,1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-isoquinolinium benzenesulfonate

1075727-06-8
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Yield: 100%

Reaction Conditions:

with trifluoroacetic acid at 0 - 5; for 0.333333 h;Product distribution / selectivity;

Steps:

18.a
( 1 R-cis)- 1 -[(3 ,4-dimethoxyphenyl)methyl] - 1 ,2,3 ,4-tetrahydro-6,7-dimethoxy-2 -methyl -2- tert-butoxycarbonylethyl-isoquinolinium besylate (I g, HPLC purity 99.0%) was added to TFA (2.5 ml), cooled to 0-5°C, and the reaction mixture was stirred for 20 minutes. Then, TFA was removed from the reaction mixture to dryness at 30-40°C under reduced pressure to afford ( 1 R-cis)- 1 - [(3 ,4-dimethoxyphenyl)methyl]- 1 ,2,3 ,4-tetrahydro-6,7-dimethoxy-2- methyl-2-carboxyethyl-isoquinolinium besylate, 0.91 g, (100% yield); HPLC purity: 97.1% with 0.56% of trans-isomer.

References:

CHEMAGIS LTD. WO2008/132748, 2008, A1 Location in patent:Page/Page column 39