(E)-3-[(1R)-1,2,3,4-tetrahydroisoquinol-1-yl]-1-[(1R,2R)-2-hydroxy-1,2-dicyclohexylethyl]oxy-1-propene

Base Information

• Chemical Name: (E)-3-[(1R)-1,2,3,4-tetrahydroisoquinol-1-yl]-1-[(1R,2R)-2-hydroxy-1,2-dicyclohexylethyl]oxy-1-propene
• CAS No.: 341544-03-4
• Molecular Formula: C₂₆H₃₉NO₂
• Molecular Weight: 397.601

Synonyms:(E)-3-[(1R)-1,2,3,4-tetrahydroisoquinol-1-yl]-1-[(1R,2R)-2-hydroxy-1,2-dicyclohexylethyl]oxy-1-propene

Chemical Property of (E)-3-[(1R)-1,2,3,4-tetrahydroisoquinol-1-yl]-1-[(1R,2R)-2-hydroxy-1,2-dicyclohexylethyl]oxy-1-propene

Chemical Property:

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Technology Process of (E)-3-[(1R)-1,2,3,4-tetrahydroisoquinol-1-yl]-1-[(1R,2R)-2-hydroxy-1,2-dicyclohexylethyl]oxy-1-propene

There total 2 articles about (E)-3-[(1R)-1,2,3,4-tetrahydroisoquinol-1-yl]-1-[(1R,2R)-2-hydroxy-1,2-dicyclohexylethyl]oxy-1-propene 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:

3,4-dihydroisoquinoline (3230-65-7) + acrolein (R,R)-1,2-dicyclohexylethylene acetal (257861-22-6) → (Z)-3-[1,2,3,4-tetrahydroisoquinol-1-yl]-1-[(1R,2R)-2-hydroxy-1,2-dicyclohexylethyl]oxy-1-propene + (E)-3-[(1R)-1,2,3,4-tetrahydroisoquinol-1-yl]-1-[(1R,2R)-2-hydroxy-1,2-dicyclohexylethyl]oxy-1-propene (341544-03-4)

Guidance literature:

acrolein (R,R)-1,2-dicyclohexylethylene acetal; With isopropylmagnesium chloride; In diethyl ether; at -50 - -40 ℃; for 1.5h;

3,4-dihydroisoquinoline; In diethyl ether; at -40 - 20 ℃; for 4h; Further stages.;

DOI:10.1021/ja004140k

Reference yield:

(1R,2R)-1,2-dicyclohexyl-1,2-ethanediol (120850-92-2) → (E)-3-[(1R)-1,2,3,4-tetrahydroisoquinol-1-yl]-1-[(1R,2R)-2-hydroxy-1,2-dicyclohexylethyl]oxy-1-propene (341544-03-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 95 percent / p-toluenesulfonic acid hydrate / CH₂Cl₂ / 2 h / 20 °C

2.1: Ti(O-i-Pr)4; i-PrMgCl / diethyl ether / 1.5 h / -50 - -40 °C

2.2: diethyl ether / 4 h / -40 - 20 °C

With isopropylmagnesium chloride; toluene-4-sulfonic acid; In diethyl ether; dichloromethane;

DOI:10.1021/ja004140k

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + (E)-3-[(1R)-1,2,3,4-tetrahydroisoquinol-1-yl]-1-[(1R,2R)-2-hydroxy-1,2-dicyclohexylethyl]oxy-1-propene (341544-03-4) → (R)-1-[(E)-3-((1R,2R)-1,2-Dicyclohexyl-2-hydroxy-ethoxy)-allyl]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Guidance literature:

With triethylamine; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1021/ja004140k

upstream raw materials:

3,4-dihydroisoquinoline

acrolein (R,R)-1,2-dicyclohexylethylene acetal

(1R,2R)-1,2-dicyclohexyl-1,2-ethanediol

Downstream raw materials:

(+)-(10bR)-1,2,3,5,6,10b-Hexahydropyrrolo-<2,1-a>isoquinoline

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