6-benzyloxy-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Base Information

Chemical Name:6-benzyloxy-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester
CAS No.:918896-64-7
Molecular Formula:C₃₀H₄₅NO₅Si
Molecular Weight:527.777
Hs Code.:

Synonyms:6-benzyloxy-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

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Chemical Property of 6-benzyloxy-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

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Technology Process of 6-benzyloxy-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

There total 13 articles about 6-benzyloxy-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

: 918896-63-6
6-benzyloxy-1-(2-hydroxy-ethyl)-7-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

: 18162-48-6
tert-butyldimethylsilyl chloride

: 918896-64-7
6-benzyloxy-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Guidance literature:: With 1H-imidazole; In dichloromethane; at 0 ℃;
DOI:10.1016/j.tet.2006.09.056

Reference yield:

: 918896-59-0
1-benzyloxy-4-bromo-2-methoxy-5-(2-nitro ethyl)benzene

: 918896-64-7
6-benzyloxy-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: lithium aluminum hydride / tetrahydrofuran / 20 °C

2: 1.90 g / tetrahydrofuran; H₂O / 4 h / 20 °C

3: 89 percent / triethylamine; poly(ethylene glycol) / palladium(II) acetate / 18 h / 80 °C

4: TFA / CH₂Cl₂ / 0 - 20 °C

5: sodium carbonate / CH₂Cl₂ / 12 h

6: 1.0 g / CH₂Cl₂ / 4 h

7: 87 percent / LiCl; sodium borohydride / ethanol; tetrahydrofuran / 0 - 20 °C

8: 82 percent / imidazole / CH₂Cl₂ / 0 °C

With 1H-imidazole; sodium tetrahydroborate; lithium aluminium tetrahydride; sodium carbonate; ethylene glycol; triethylamine; trifluoroacetic acid; lithium chloride; poly(ethylene glycol); palladium diacetate; In tetrahydrofuran; ethanol; dichloromethane; water; 3: Heck reaction / 5: Michael reaction;
DOI:10.1016/j.tet.2006.09.056

Reference yield:

: 918896-60-3
2-[2-bromo-4-methoxy-5-benzyloxy]-1-(tert-butoxycarbonyl amino)-ethane

: 918896-64-7
6-benzyloxy-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 89 percent / triethylamine; poly(ethylene glycol) / palladium(II) acetate / 18 h / 80 °C

2: TFA / CH₂Cl₂ / 0 - 20 °C

3: sodium carbonate / CH₂Cl₂ / 12 h

4: 1.0 g / CH₂Cl₂ / 4 h

5: 87 percent / LiCl; sodium borohydride / ethanol; tetrahydrofuran / 0 - 20 °C

6: 82 percent / imidazole / CH₂Cl₂ / 0 °C

With 1H-imidazole; sodium tetrahydroborate; sodium carbonate; ethylene glycol; triethylamine; trifluoroacetic acid; lithium chloride; poly(ethylene glycol); palladium diacetate; In tetrahydrofuran; ethanol; dichloromethane; 1: Heck reaction / 3: Michael reaction;
DOI:10.1016/j.tet.2006.09.056