(1R,3R)-N-benzyl-6-methoxy-8-isopropoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline

Base Information

Chemical Name:(1R,3R)-N-benzyl-6-methoxy-8-isopropoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline
CAS No.:765253-06-3
Molecular Formula:C₂₂H₂₉NO₂
Molecular Weight:339.478
Hs Code.:

Synonyms:(1R,3R)-N-benzyl-6-methoxy-8-isopropoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline

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Chemical Property of (1R,3R)-N-benzyl-6-methoxy-8-isopropoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline

Chemical Property:

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Technology Process of (1R,3R)-N-benzyl-6-methoxy-8-isopropoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline

There total 1 articles about (1R,3R)-N-benzyl-6-methoxy-8-isopropoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline 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: 87.0%

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

: 75-26-3
isopropyl bromide

: 765253-06-3
(1R,3R)-N-benzyl-6-methoxy-8-isopropoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline

Guidance literature:: With sodium hydroxide; tri-n-butylamine hydrochloride; In dichloromethane; at 20 ℃; for 168h;
DOI:10.1016/S0040-4020(97)10301-5

Reference yield: 68.0%

: 765253-06-3
(1R,3R)-N-benzyl-6-methoxy-8-isopropoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline

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

Guidance literature:: With sodium thioisopropylate; In N,N-dimethyl-formamide; for 3h; Heating;
DOI:10.1016/S0040-4020(97)10301-5

Reference yield:

: 765253-06-3
(1R,3R)-N-benzyl-6-methoxy-8-isopropoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline

: (1R,3R)-2-Benzyl-5-(5-hydroxy-4-methoxy-2-methyl-naphthalen-1-yl)-1,3-dimethyl-1,2,3,4-tetrahydro-isoquinolin-8-ol

Guidance literature:: Multi-step reaction with 8 steps

1.1: 68 percent / sodium thioisopropylate / dimethylformamide / 3 h / Heating

2.1: 71 percent / N,N-diisopropylethylamine; N,N-dimethylaminopyridine / CH₂Cl₂

3.1: 69 percent / NaOAc / (PPh₃)2PdCl₂ / N,N-dimethyl-acetamide / 100 °C

4.1: 117 mg / LiAlH₄ / tetrahydrofuran / 0.08 h

5.1: triphenylphosphine; 1,2-dibromotetrachloroethane / CH₂Cl₂ / 0.17 h

5.2: 95 percent / LiAlH₄ / tetrahydrofuran / 0.17 h / 0 °C

6.1: thallium ethanolate / CH₂Cl₂ / 0.5 h / 20 °C

6.2: CH₂Cl₂ / 0.08 h

7.1: 33.0 mg / dppp; n-Bu₃N; formic acid / (PPh₃)2PdCl₂ / dimethylformamide / 2.5 h / 100 °C

8.1: boron trifluoride / CH₂Cl₂; hexane / 5 h / -40 - -15 °C

With dmap; lithium aluminium tetrahydride; formic acid; tributyl-amine; 1,2-dibromo-1,1,2,2-tetrachloroethane; sodium thioisopropylate; 1,3-bis-(diphenylphosphino)propane; boron trifluoride; sodium acetate; thallium (I) ethoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl acetamide; N,N-dimethyl-formamide; 1.1: demethylation / 2.1: Esterification / 3.1: Cyclization / 4.1: Reduction / 5.1: halogenation / 5.2: Reduction / 6.1: Metallation / 6.2: Esterification / 7.1: Reduction / 8.1: dealkylation;
DOI:10.1016/S0040-4020(97)10301-5