(1R,3R)-2,2,2-trichloroethyl 3-<(2R,3R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-3-methoxymethoxymethylpyrrolidin-2-yl>-1-hydroxymethyl-8-methoxy-3,4-dihydro-2(1H)-isoquinolinecarboxylate

Base Information

• Chemical Name: (1R,3R)-2,2,2-trichloroethyl 3-<(2R,3R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-3-methoxymethoxymethylpyrrolidin-2-yl>-1-hydroxymethyl-8-methoxy-3,4-dihydro-2(1H)-isoquinolinecarboxylate
• CAS No.: 152500-53-3
• Molecular Formula: C₃₄H₄₅Cl₃N₂O₉
• Molecular Weight: 732.098

Synonyms:

Chemical Property of (1R,3R)-2,2,2-trichloroethyl 3-<(2R,3R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-3-methoxymethoxymethylpyrrolidin-2-yl>-1-hydroxymethyl-8-methoxy-3,4-dihydro-2(1H)-isoquinolinecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3R)-2,2,2-trichloroethyl 3-<(2R,3R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-3-methoxymethoxymethylpyrrolidin-2-yl>-1-hydroxymethyl-8-methoxy-3,4-dihydro-2(1H)-isoquinolinecarboxylate

There total 13 articles about (1R,3R)-2,2,2-trichloroethyl 3-<(2R,3R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-3-methoxymethoxymethylpyrrolidin-2-yl>-1-hydroxymethyl-8-methoxy-3,4-dihydro-2(1H)-isoquinolinecarboxylate 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:

2-bromo-3-methylanisole (38197-43-2) → (1R,3R)-2,2,2-trichloroethyl 3-<(2R,3R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-3-methoxymethoxymethylpyrrolidin-2-yl>-1-hydroxymethyl-8-methoxy-3,4-dihydro-2(1H)-isoquinolinecarboxylate (152500-53-3)

Guidance literature:

Multi-step reaction with 12 steps

1: 99 percent / n-butyllihium / hexane; diethyl ether / 0.75 h / -78 °C

2: 98 percent / pyridine, chromium (VI) oxide / CH₂Cl₂ / 0.75 h / Ambient temperature

3: 98 percent / hydrogen / 20percent Pd/C / methanol / 15 h / 760 Torr / Ambient temperature

4: 92 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 17 h / Ambient temperature

5: 51 percent / lithium diisopropylamide, N,N,N',N'-tetramethylethylenediamine / tetrahydrofuran; hexane / 2 h / -78 °C

6: 42 percent / 2.6 M Jones reagent, celite / acetone / 0.33 h / Ambient temperature

7: 67 percent / 38percent ammonia / H₂O; tetrahydrofuran / 15 h / Ambient temperature

8: 93 percent / sodium borohydride, 37percent hydrochloric acid / methanol; H₂O / 2 h / 0 °C

9: 85 percent / pyridine / 15 h / Ambient temperature

10: 86 percent / ferric chloride on silica gel / CHCl₃ / 15 h / Ambient temperature

11: sodium periodate / methanol; H₂O / 12 h / Ambient temperature

12: NaBH₄ / methanol; H₂O / 0.5 h / Ambient temperature

With pyridine; chromium(VI) oxide; hydrogenchloride; ammonium hydroxide; sodium tetrahydroborate; sodium periodate; iron(III) chloride on silica; n-butyllithium; jones reagent; N,N,N,N,-tetramethylethylenediamine; Celite; hydrogen; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; chloroform; water; acetone;

DOI:10.1016/S0040-4020(01)80644-X

Reference yield:

2-<1-<(4R,5R)-5-benzyloxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl>-1-hydroxymethyl>-3-methylanisole → (1R,3R)-2,2,2-trichloroethyl 3-<(2R,3R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-3-methoxymethoxymethylpyrrolidin-2-yl>-1-hydroxymethyl-8-methoxy-3,4-dihydro-2(1H)-isoquinolinecarboxylate (152500-53-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 98 percent / pyridine, chromium (VI) oxide / CH₂Cl₂ / 0.75 h / Ambient temperature

2: 98 percent / hydrogen / 20percent Pd/C / methanol / 15 h / 760 Torr / Ambient temperature

3: 92 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 17 h / Ambient temperature

4: 51 percent / lithium diisopropylamide, N,N,N',N'-tetramethylethylenediamine / tetrahydrofuran; hexane / 2 h / -78 °C

5: 42 percent / 2.6 M Jones reagent, celite / acetone / 0.33 h / Ambient temperature

6: 67 percent / 38percent ammonia / H₂O; tetrahydrofuran / 15 h / Ambient temperature

7: 93 percent / sodium borohydride, 37percent hydrochloric acid / methanol; H₂O / 2 h / 0 °C

8: 85 percent / pyridine / 15 h / Ambient temperature

9: 86 percent / ferric chloride on silica gel / CHCl₃ / 15 h / Ambient temperature

10: sodium periodate / methanol; H₂O / 12 h / Ambient temperature

11: NaBH₄ / methanol; H₂O / 0.5 h / Ambient temperature

With pyridine; chromium(VI) oxide; hydrogenchloride; ammonium hydroxide; sodium tetrahydroborate; sodium periodate; iron(III) chloride on silica; jones reagent; N,N,N,N,-tetramethylethylenediamine; Celite; hydrogen; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; chloroform; water; acetone;

DOI:10.1016/S0040-4020(01)80644-X

Reference yield:

2-<(4R,5R)-5-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-4-carbonyl>-3-methylanisole (152500-41-9) → (1R,3R)-2,2,2-trichloroethyl 3-<(2R,3R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-3-methoxymethoxymethylpyrrolidin-2-yl>-1-hydroxymethyl-8-methoxy-3,4-dihydro-2(1H)-isoquinolinecarboxylate (152500-53-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 98 percent / hydrogen / 20percent Pd/C / methanol / 15 h / 760 Torr / Ambient temperature

2: 92 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 17 h / Ambient temperature

3: 51 percent / lithium diisopropylamide, N,N,N',N'-tetramethylethylenediamine / tetrahydrofuran; hexane / 2 h / -78 °C

4: 42 percent / 2.6 M Jones reagent, celite / acetone / 0.33 h / Ambient temperature

5: 67 percent / 38percent ammonia / H₂O; tetrahydrofuran / 15 h / Ambient temperature

6: 93 percent / sodium borohydride, 37percent hydrochloric acid / methanol; H₂O / 2 h / 0 °C

7: 85 percent / pyridine / 15 h / Ambient temperature

8: 86 percent / ferric chloride on silica gel / CHCl₃ / 15 h / Ambient temperature

9: sodium periodate / methanol; H₂O / 12 h / Ambient temperature

10: NaBH₄ / methanol; H₂O / 0.5 h / Ambient temperature

With pyridine; hydrogenchloride; ammonium hydroxide; sodium tetrahydroborate; sodium periodate; iron(III) chloride on silica; jones reagent; N,N,N,N,-tetramethylethylenediamine; Celite; hydrogen; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; chloroform; water; acetone;

DOI:10.1016/S0040-4020(01)80644-X

upstream raw materials:

2-bromo-3-methylanisole

2-<(4S,5R)-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane-4-carbonyl>-3-methylanisole

2-<(4S,5R)-5-methoxymethoxymethyl-2,2-dimethyl-1,3-dioxolane-4-carbonyl>-3-methylanisole

2-<(4R,5R)-5-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-4-carbonyl>-3-methylanisole

Downstream raw materials:

(-)-quinocarcin

<5R-(5α,7β,8β,10β,11β,11aβ)>-7-cyano-5,7,8,9,10,11,11a,12-octahydro-4-methoxy-5-(hydroxymethyl)-13-methyl-8,11-iminoazepino<1,2-b>isoquinoline-10-carboxylic acid

(1R,3R)-2,2,2-trichloroethyl 1-acetoxymethyl-3-<(2R,3R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-3-methoxymethoxymethylpyrrolidin-2-yl>-8-methoxy-3,4-dihydro-2(1H)-isoquinolinecarboxylate

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