(1R,3R)-(N-benzyl-8-isopropoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-6-yl) 1'-bromo-5'-isopropoxy-4'-methoxy-2'-naphthoate

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Chemical Name:(1R,3R)-(N-benzyl-8-isopropoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-6-yl) 1'-bromo-5'-isopropoxy-4'-methoxy-2'-naphthoate
CAS No.:202215-77-8
Molecular Formula:C₃₆H₄₀BrNO₅
Molecular Weight:646.621
Hs Code.:

Synonyms:(1R,3R)-(N-benzyl-8-isopropoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-6-yl) 1'-bromo-5'-isopropoxy-4'-methoxy-2'-naphthoate

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Chemical Property of (1R,3R)-(N-benzyl-8-isopropoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-6-yl) 1'-bromo-5'-isopropoxy-4'-methoxy-2'-naphthoate

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Technology Process of (1R,3R)-(N-benzyl-8-isopropoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-6-yl) 1'-bromo-5'-isopropoxy-4'-methoxy-2'-naphthoate

There total 9 articles about (1R,3R)-(N-benzyl-8-isopropoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-6-yl) 1'-bromo-5'-isopropoxy-4'-methoxy-2'-naphthoate 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: 71.0%

: 218956-26-4
(1R,3R)-N-benzyl-6-hydroxy-8-isopropoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline

: 1-bromo-5-isopropoxy-4-methoxy-naphthalene-2-carbonyl chloride

: 202215-77-8
(1R,3R)-(N-benzyl-8-isopropoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-6-yl) 1'-bromo-5'-isopropoxy-4'-methoxy-2'-naphthoate

Guidance literature:: With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane;
DOI:10.1016/S0040-4020(97)10301-5

Reference yield:

: 162147-18-4
Ethyl 8-bromo-5-isopropoxy-4-methoxy-2-naphthoate

: 202215-77-8
(1R,3R)-(N-benzyl-8-isopropoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-6-yl) 1'-bromo-5'-isopropoxy-4'-methoxy-2'-naphthoate

Guidance literature:: Multi-step reaction with 7 steps

1: H₂; Et₃N / Pd/C / methanol / 15 h / 3750.3 Torr

2: 7.77 g / LiAlH₄ / tetrahydrofuran / 1.5 h / Heating

3: 95 percent / NaOAc; N(n-Bu)4Br₃ / CH₂Cl₂ / 1 h / 0 °C

4: 90 percent / MnO₂ / CH₂Cl₂ / 1.5 h / Heating

5: 98 percent / NaClO₂; sulphamic acid; NaOAc / acetic acid; H₂O; dioxane / 4 h / 20 °C

6: DMF; oxalyl chloride / CH₂Cl₂ / 0.5 h / 20 °C

7: 71 percent / N,N-diisopropylethylamine; N,N-dimethylaminopyridine / CH₂Cl₂

With dmap; manganese(IV) oxide; sodium chlorite; lithium aluminium tetrahydride; oxalyl dichloride; aminosulfonic acid; hydrogen; sodium acetate; tetra-N-butylammonium tribromide; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; acetic acid; 1: Hydrogenation / 2: Reduction / 3: Bromination / 4: Oxidation / 5: Oxidation / 6: Chlorination / 7: Esterification;
DOI:10.1016/S0040-4020(97)10301-5

Reference yield:

: (1R,3R)-2-Benzyl-6-methoxy-1,3-dimethyl-1,2,3,4-tetrahydro-isoquinolin-8-ol

: 202215-77-8
(1R,3R)-(N-benzyl-8-isopropoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-6-yl) 1'-bromo-5'-isopropoxy-4'-methoxy-2'-naphthoate

Guidance literature:: Multi-step reaction with 3 steps

1: 87 percent / aq. NaOH; Bu₃N*HCl / CH₂Cl₂ / 168 h / 20 °C

2: 68 percent / sodium thioisopropylate / dimethylformamide / 3 h / Heating

3: 71 percent / N,N-diisopropylethylamine; N,N-dimethylaminopyridine / CH₂Cl₂

With dmap; sodium hydroxide; sodium thioisopropylate; tri-n-butylamine hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; 1: Etherification / 2: demethylation / 3: Esterification;
DOI:10.1016/S0040-4020(97)10301-5