ChemicalBook CAS DataBase List (R)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

(R)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline synthesis

15synthesis methods

Product Name:(R)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
CAS Number:85-63-2
Molecular formula:C21H27NO4
Molecular Weight:357.44

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(R)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

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Yield: 95.51%

Reaction Conditions:

Stage #1:formaldehyd;(-) N-norlaudanosine with disodium hydrogen phosphite pentahydrate in tetrahydrofuranReflux;
Stage #2: with (R)-Mandelic Acid in methanolReflux;

Steps:

11
Weigh 1000 g of 6,7-dimethoxy-1-(R)-3,4-dimethoxybenzyl-1,2,3,4-tetrahydroisoquinoline,2000 g of disodium hydrogen phosphite pentahydrate, 10.0 L of 38% formaldehyde solution and 8.0 L of tetrahydrofuran were added, and the reaction was refluxed until the reaction was completed.After cooling to room temperature, the organic phase was separated, the aqueous phase was extracted with dichloromethane,After adding methanol to dissolve, 600 g of D-mandelic acid was further added, and the mixture was refluxed under stirring until the reaction was completed.The crystals were stirred and cooled, and filtered.The filter cake is dissolved in water, and the pH of the aqueous sodium hydroxide solution is adjusted to 10, and extracted with dichloromethane.Concentration gave 990 g of 6,7-dimethoxy-2-methyl-1-(R)-3,4-dimethoxybenzyl-1,2,3,4-tetrahydroisoquinoline.The yield was calculated to be 95.51%, the optical purity was 99.92%, and the chemical purity was 99.50%.

References:

SICHUAN CREDIT PHARMACEUTICAL CO LTD;Sichuan Keruide Pharmaceutical Co., Ltd.;QIN YONG;Qin Yong;FU LIN;Fu Lin;SU LEI;Su Lei;CHEN GANG;Chen Gang;LI XIAOLI;Li Xiaoli CN107778234, 2018, A Location in patent:Paragraph 0066