(1R,3S)-3-((2R,5S)-5-Benzyloxymethyl-1-tert-butoxycarbonyl-pyrrolidin-2-yl)-1-formyl-8-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid 2,2,2-trichloro-ethyl ester

Base Information

• Chemical Name: (1R,3S)-3-((2R,5S)-5-Benzyloxymethyl-1-tert-butoxycarbonyl-pyrrolidin-2-yl)-1-formyl-8-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid 2,2,2-trichloro-ethyl ester
• CAS No.: 154978-03-7
• Molecular Formula: C₃₁H₃₇Cl₃N₂O₇
• Molecular Weight: 656.003
• Mol file: 154978-03-7.mol

Synonyms:

Chemical Property of (1R,3S)-3-((2R,5S)-5-Benzyloxymethyl-1-tert-butoxycarbonyl-pyrrolidin-2-yl)-1-formyl-8-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid 2,2,2-trichloro-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3S)-3-((2R,5S)-5-Benzyloxymethyl-1-tert-butoxycarbonyl-pyrrolidin-2-yl)-1-formyl-8-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid 2,2,2-trichloro-ethyl ester

There total 11 articles about (1R,3S)-3-((2R,5S)-5-Benzyloxymethyl-1-tert-butoxycarbonyl-pyrrolidin-2-yl)-1-formyl-8-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid 2,2,2-trichloro-ethyl 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:

2-bromo-3-methylanisole (38197-43-2) → (1R,3S)-3-((2R,5S)-5-Benzyloxymethyl-1-tert-butoxycarbonyl-pyrrolidin-2-yl)-1-formyl-8-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid 2,2,2-trichloro-ethyl ester (154978-03-7)

Guidance literature:

Multi-step reaction with 10 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: 48 percent / lithium diisopropylamide, N,N,N',N'-tetramethylethylenediamine / tetrahydrofuran; hexane / 2 h / -78 °C

6: 68 percent / 2.6 M Jones reagent, celite / acetone / 0.33 h / Ambient temperature

7: 72 percent / 38percent ammonia / H₂O; tetrahydrofuran / 15 h / Ambient temperature

8: 98 percent / sodium borohydride, 37percent hydrochloric acid / methanol; H₂O / 2 h / 0 °C

9: 88 percent / pyridine / 15 h / Ambient temperature

10: 1.) 37percent hydrochloric acid; 2.) NaIO₄ / 1.) water, methanol, room temp., 5 h; 2.) water, methanol, room temp., 15 h

With pyridine; chromium(VI) oxide; hydrogenchloride; ammonium hydroxide; sodium tetrahydroborate; sodium periodate; 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; 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,3S)-3-((2R,5S)-5-Benzyloxymethyl-1-tert-butoxycarbonyl-pyrrolidin-2-yl)-1-formyl-8-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid 2,2,2-trichloro-ethyl ester (154978-03-7)

Guidance literature:

Multi-step reaction with 9 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: 48 percent / lithium diisopropylamide, N,N,N',N'-tetramethylethylenediamine / tetrahydrofuran; hexane / 2 h / -78 °C

5: 68 percent / 2.6 M Jones reagent, celite / acetone / 0.33 h / Ambient temperature

6: 72 percent / 38percent ammonia / H₂O; tetrahydrofuran / 15 h / Ambient temperature

7: 98 percent / sodium borohydride, 37percent hydrochloric acid / methanol; H₂O / 2 h / 0 °C

8: 88 percent / pyridine / 15 h / Ambient temperature

9: 1.) 37percent hydrochloric acid; 2.) NaIO₄ / 1.) water, methanol, room temp., 5 h; 2.) water, methanol, room temp., 15 h

With pyridine; chromium(VI) oxide; hydrogenchloride; ammonium hydroxide; sodium tetrahydroborate; sodium periodate; 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; 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,3S)-3-((2R,5S)-5-Benzyloxymethyl-1-tert-butoxycarbonyl-pyrrolidin-2-yl)-1-formyl-8-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid 2,2,2-trichloro-ethyl ester (154978-03-7)

Guidance literature:

Multi-step reaction with 8 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: 48 percent / lithium diisopropylamide, N,N,N',N'-tetramethylethylenediamine / tetrahydrofuran; hexane / 2 h / -78 °C

4: 68 percent / 2.6 M Jones reagent, celite / acetone / 0.33 h / Ambient temperature

5: 72 percent / 38percent ammonia / H₂O; tetrahydrofuran / 15 h / Ambient temperature

6: 98 percent / sodium borohydride, 37percent hydrochloric acid / methanol; H₂O / 2 h / 0 °C

7: 88 percent / pyridine / 15 h / Ambient temperature

8: 1.) 37percent hydrochloric acid; 2.) NaIO₄ / 1.) water, methanol, room temp., 5 h; 2.) water, methanol, room temp., 15 h

With pyridine; hydrogenchloride; ammonium hydroxide; sodium tetrahydroborate; sodium periodate; 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; water; acetone;

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

upstream raw materials:

(1R,3S)-3-((2R,5S)-5-Benzyloxymethyl-1-tert-butoxycarbonyl-pyrrolidin-2-yl)-8-methoxy-1-((1R,2R)-1,2,3-trihydroxy-propyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid 2,2,2-trichloro-ethyl ester

(1R,3R)-2,2,2-trichloroethyl 3-<(2R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonylpyrrolidin-2-yl>-1-<(4R,5R)-5-methoxymethoxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl>-8-methoxy-3,4-dihydro-2(1H)-isoquinolinecarboxylate

2-bromo-3-methylanisole

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

Downstream raw materials:

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

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