8-hydroxy-1-[4-(2-isopropoxy-5-methoxycarbonyl-phenoxy)-benzyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Base Information

Chemical Name:8-hydroxy-1-[4-(2-isopropoxy-5-methoxycarbonyl-phenoxy)-benzyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester
CAS No.:454185-88-7
Molecular Formula:C₃₄H₄₁NO₉
Molecular Weight:607.701
Hs Code.:

8-hydroxy-1-[4-(2-isopropoxy-5-methoxycarbonyl-phenoxy)-benzyl]-6,7-dimethoxy-3,4-dihydro-1<i>H</i>-isoquinoline-2-carboxylic acid <i>tert</i>-butyl ester

Synonyms:8-hydroxy-1-[4-(2-isopropoxy-5-methoxycarbonyl-phenoxy)-benzyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

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Chemical Property of 8-hydroxy-1-[4-(2-isopropoxy-5-methoxycarbonyl-phenoxy)-benzyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

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Technology Process of 8-hydroxy-1-[4-(2-isopropoxy-5-methoxycarbonyl-phenoxy)-benzyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

There total 32 articles about 8-hydroxy-1-[4-(2-isopropoxy-5-methoxycarbonyl-phenoxy)-benzyl]-6,7-dimethoxy-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:

: 7632-62-4
3-benzyloxy-4,5-dimethoxybenzyl alcohol

: 454185-88-7
8-hydroxy-1-[4-(2-isopropoxy-5-methoxycarbonyl-phenoxy)-benzyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: SOCl₂ / benzene / 12 h / 20 °C

1.2: dimethylsulfoxide; benzene / 20 °C

2.1: 98 percent / sodium hydroxide / ethanol / 20 h / Heating

3.1: oxalyl chloride / benzene / 2 h / 20 °C

4.1: sodium hydroxide / H₂O; CH₂Cl₂ / 1 h / 20 °C

5.1: B₂H₆*THF; BF₃*Et₂O / tetrahydrofuran / Heating

5.2: 98 percent / hydrochloric acid / H₂O; tetrahydrofuran

6.1: 73 percent / 1-hydroxybenzotriazole hydrate; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide / 48 h / 0 °C

7.1: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 0 °C

8.1: Dess-Martin periodinane / 1 h

9.1: NaClO₂; Na₂HPO₄; resorcinol / dimethylsulfoxide / 12 h / 20 °C

10.1: methanol; benzene / 1 h / 20 °C

11.1: POCl₃ / benzene / 12 h / Heating

11.2: 40 percent / sodium borohydride / methanol / 5 h / -78 °C

12.1: hydrogen; hydrochloric acid / Pd/C / ethanol; ethyl acetate; H₂O / 15 h / 20 °C

13.1: triethylamine / 12 h / -78 - 20 °C

With hydrogenchloride; sodium hydroxide; sodium chlorite; disodium hydrogenphosphate; thionyl chloride; oxalyl dichloride; B₂H₆-THF; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; Dess-Martin periodane; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; recorcinol; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; benzene; 4.1: Schotten-Baumann reaction / 8.1: Dess-Martin oxidation / 11.1: Bischler-Napieralski cyclization;
DOI:10.1021/ol0261635

Reference yield:

: 2973-76-4
5-bromo-4-hydroxy-3-methoxybenzaldehyde

: 454185-88-7
8-hydroxy-1-[4-(2-isopropoxy-5-methoxycarbonyl-phenoxy)-benzyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 19 steps

1.1: 89 percent / sodium hydroxide; Adogen 464(R) / CH₂Cl₂ / 15 h / 20 °C

2.1: sodium borohydride / tetrahydrofuran; methanol / 2 h

3.1: imidazole / dimethylformamide / 12 h / 20 °C

4.1: n-butyllithium / 1 h / -78 °C

4.2: trimethyl borate / 12 h / -78 - 20 °C

4.3: 78 percent / hydrogen peroxide / 12 h / 20 °C

5.1: 75 percent / potassium carbonate / acetone / 12 h / Heating

6.1: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h / 0 °C

7.1: SOCl₂ / benzene / 12 h / 20 °C

7.2: dimethylsulfoxide; benzene / 20 °C

8.1: 98 percent / sodium hydroxide / ethanol / 20 h / Heating

9.1: oxalyl chloride / benzene / 2 h / 20 °C

10.1: sodium hydroxide / H₂O; CH₂Cl₂ / 1 h / 20 °C

11.1: B₂H₆*THF; BF₃*Et₂O / tetrahydrofuran / Heating

11.2: 98 percent / hydrochloric acid / H₂O; tetrahydrofuran

12.1: 73 percent / 1-hydroxybenzotriazole hydrate; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide / 48 h / 0 °C

13.1: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 0 °C

14.1: Dess-Martin periodinane / 1 h

15.1: NaClO₂; Na₂HPO₄; resorcinol / dimethylsulfoxide / 12 h / 20 °C

16.1: methanol; benzene / 1 h / 20 °C

17.1: POCl₃ / benzene / 12 h / Heating

17.2: 40 percent / sodium borohydride / methanol / 5 h / -78 °C

18.1: hydrogen; hydrochloric acid / Pd/C / ethanol; ethyl acetate; H₂O / 15 h / 20 °C

19.1: triethylamine / 12 h / -78 - 20 °C

With 1H-imidazole; hydrogenchloride; sodium hydroxide; sodium chlorite; sodium tetrahydroborate; disodium hydrogenphosphate; n-butyllithium; thionyl chloride; oxalyl dichloride; B₂H₆-THF; Adogen 464(R); boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; Dess-Martin periodane; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; recorcinol; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetone; benzene; 10.1: Schotten-Baumann reaction / 14.1: Dess-Martin oxidation / 17.1: Bischler-Napieralski cyclization;
DOI:10.1021/ol0261635

Reference yield:

: 14199-15-6
Methyl 4-hydroxyphenylacetate

: 454185-88-7
8-hydroxy-1-[4-(2-isopropoxy-5-methoxycarbonyl-phenoxy)-benzyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / -40 °C

2.1: 85 percent / potassium acetate; PdCl₂(dppf) / dioxane / 80 °C

3.1: diethanolamine / propan-2-ol; diethyl ether

3.2: hydrochloric acid / H₂O; tetrahydrofuran / 20 °C

4.1: 57 percent / copper(II) acetate; pyridine; molecular sieves 4 Angstroem / CH₂Cl₂ / 48 h / 20 °C

5.1: 100 percent / lithium hydroxide / methanol; tetrahydrofuran; H₂O / 2 h / 20 °C

6.1: 73 percent / 1-hydroxybenzotriazole hydrate; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide / 48 h / 0 °C

7.1: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 0 °C

8.1: Dess-Martin periodinane / 1 h

9.1: NaClO₂; Na₂HPO₄; resorcinol / dimethylsulfoxide / 12 h / 20 °C

10.1: methanol; benzene / 1 h / 20 °C

11.1: POCl₃ / benzene / 12 h / Heating

11.2: 40 percent / sodium borohydride / methanol / 5 h / -78 °C

12.1: hydrogen; hydrochloric acid / Pd/C / ethanol; ethyl acetate; H₂O / 15 h / 20 °C

13.1: triethylamine / 12 h / -78 - 20 °C

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; lithium hydroxide; sodium chlorite; disodium hydrogenphosphate; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; potassium acetate; copper diacetate; Dess-Martin periodane; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 2,2'-iminobis[ethanol]; recorcinol; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol; benzene; 8.1: Dess-Martin oxidation / 11.1: Bischler-Napieralski cyclization;
DOI:10.1021/ol0261635