(2S,5R)-2-Benzyloxymethyl-5-((1R,5S,10bR)-1-hydroxymethyl-10-methoxy-3-oxo-1,5,6,10b-tetrahydro-oxazolo[4,3-a]isoquinolin-5-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (2S,5R)-2-Benzyloxymethyl-5-((1R,5S,10bR)-1-hydroxymethyl-10-methoxy-3-oxo-1,5,6,10b-tetrahydro-oxazolo[4,3-a]isoquinolin-5-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS No.: 159453-40-4
• Molecular Formula: C₃₀H₃₈N₂O₇
• Molecular Weight: 538.641
• Mol file: 159453-40-4.mol

Synonyms:

Chemical Property of (2S,5R)-2-Benzyloxymethyl-5-((1R,5S,10bR)-1-hydroxymethyl-10-methoxy-3-oxo-1,5,6,10b-tetrahydro-oxazolo[4,3-a]isoquinolin-5-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5R)-2-Benzyloxymethyl-5-((1R,5S,10bR)-1-hydroxymethyl-10-methoxy-3-oxo-1,5,6,10b-tetrahydro-oxazolo[4,3-a]isoquinolin-5-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 16 articles about (2S,5R)-2-Benzyloxymethyl-5-((1R,5S,10bR)-1-hydroxymethyl-10-methoxy-3-oxo-1,5,6,10b-tetrahydro-oxazolo[4,3-a]isoquinolin-5-yl)-pyrrolidine-1-carboxylic acid tert-butyl 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) → (2S,5R)-2-Benzyloxymethyl-5-((1R,5S,10bR)-1-hydroxymethyl-10-methoxy-3-oxo-1,5,6,10b-tetrahydro-oxazolo[4,3-a]isoquinolin-5-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (159453-40-4)

Guidance literature:

Multi-step reaction with 13 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: triethylamine / CHCl₃ / 3 h / Ambient temperature

10: 37percent hydrochloric acid / methanol; H₂O / 3 h / Ambient temperature

11: sodium hydroxide / ethanol / 3 h / Ambient temperature

12: sodium periodate / methanol; H₂O / 13 h / Ambient temperature

13: sodium borohydride / methanol; H₂O / 0.5 h / Ambient temperature

With pyridine; chromium(VI) oxide; hydrogenchloride; ammonium hydroxide; sodium hydroxide; sodium tetrahydroborate; sodium periodate; n-butyllithium; jones reagent; N,N,N,N,-tetramethylethylenediamine; Celite; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; 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) → (2S,5R)-2-Benzyloxymethyl-5-((1R,5S,10bR)-1-hydroxymethyl-10-methoxy-3-oxo-1,5,6,10b-tetrahydro-oxazolo[4,3-a]isoquinolin-5-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (159453-40-4)

Guidance literature:

Multi-step reaction with 11 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: triethylamine / CHCl₃ / 3 h / Ambient temperature

8: 37percent hydrochloric acid / methanol; H₂O / 3 h / Ambient temperature

9: sodium hydroxide / ethanol / 3 h / Ambient temperature

10: sodium periodate / methanol; H₂O / 13 h / Ambient temperature

11: sodium borohydride / methanol; H₂O / 0.5 h / Ambient temperature

With hydrogenchloride; ammonium hydroxide; sodium hydroxide; sodium tetrahydroborate; sodium periodate; jones reagent; N,N,N,N,-tetramethylethylenediamine; Celite; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; 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 → (2S,5R)-2-Benzyloxymethyl-5-((1R,5S,10bR)-1-hydroxymethyl-10-methoxy-3-oxo-1,5,6,10b-tetrahydro-oxazolo[4,3-a]isoquinolin-5-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (159453-40-4)

Guidance literature:

Multi-step reaction with 12 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: triethylamine / CHCl₃ / 3 h / Ambient temperature

9: 37percent hydrochloric acid / methanol; H₂O / 3 h / Ambient temperature

10: sodium hydroxide / ethanol / 3 h / Ambient temperature

11: sodium periodate / methanol; H₂O / 13 h / Ambient temperature

12: sodium borohydride / methanol; H₂O / 0.5 h / Ambient temperature

With pyridine; chromium(VI) oxide; hydrogenchloride; ammonium hydroxide; sodium hydroxide; sodium tetrahydroborate; sodium periodate; jones reagent; N,N,N,N,-tetramethylethylenediamine; Celite; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; 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