(1R,2R)-1-[(3,4-Dimethoxyphenyl)methyl]-2-[3-(tert-butoxy)-3-oxopropyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinolinium benzenesulfonate synthesis
- Product Name:(1R,2R)-1-[(3,4-Dimethoxyphenyl)methyl]-2-[3-(tert-butoxy)-3-oxopropyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinolinium benzenesulfonate
- CAS Number:1075727-00-2
- Molecular formula:C34H45NO9S
- Molecular Weight:643.79
Yield:-
Reaction Conditions:
Stage #1:(1R)-1-[(3,4-dimethoxyphenyl)-methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-tert-butoxycarbonylethyl-isoquinoline oxalate with sodium hydroxide in water;toluene; pH=7
Stage #2:Methyl benzenesulfonate in ethyl acetate at 20; for 10 h;Temperature;Solvent;Reagent/catalyst;
Steps:
2.4-2.8; 3.4-3.8
Step 4: Dissolve the R-alkali condensate oxalate in 10 times the amount of water to dissolve, extract with 10 times the amount of toluene, adjust the pH>7 by sodium hydroxide solution, and stir to separate the water layer;Step 5: The organic layer was concentrated to dryness under reduced pressure at 80°C; add 1 times the amount of methyl benzenesulfonate and 1 times the amount of ethyl acetate to the system, and stir at 20°C for 10 hours; Add 10 times the amount of ether, spin off and discard the filtrate after crystallization;Step 6: Add 3 times the amount of dichloromethane to the upper step filter cake to dissolve, drop 5 times the amount of ether with stirring, crystallize, and discard the filter cake;Step 7: Concentrate the filtrate from the previous step to dryness at 30°C under reduced pressure, add 1-fold amount of dichloromethane, drop in 2-fold amount of ethyl acetate with stirring, crystallize, and discard the filtrate;Step 8: The filter cake is concentrated to dryness under reduced pressure at a temperature of 40°C to obtain R,R′-cis ester.
References:
Shangyao Dongying (Jiangsu) Pharmaceutical Co., Ltd.;Zhou Yabing;Ding Wenming;Du Fang;Wang Xiaoyi;Zhao Min;Jiang Rongrong;Chen Haibo CN111072563, 2020, A Location in patent:Paragraph 0035; 0039-0043; 0044; 0048-0052
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