(4aR,5S,6R)-N-(3-Bromopropionyl)-5,6-epoxy-2,3-dihydro-4H,7H-10a-(benzyloxycarbonyl)quinoline

Base Information

• Chemical Name: (4aR,5S,6R)-N-(3-Bromopropionyl)-5,6-epoxy-2,3-dihydro-4H,7H-10a-(benzyloxycarbonyl)quinoline
• CAS No.: 171523-79-8
• Molecular Formula: C₂₀H₂₂BrNO₄
• Molecular Weight: 420.303
• Mol file: 171523-79-8.mol

Synonyms:(4aR,5S,6R)-N-(3-Bromopropionyl)-5,6-epoxy-2,3-dihydro-4H,7H-10a-(benzyloxycarbonyl)quinoline

Chemical Property of (4aR,5S,6R)-N-(3-Bromopropionyl)-5,6-epoxy-2,3-dihydro-4H,7H-10a-(benzyloxycarbonyl)quinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aR,5S,6R)-N-(3-Bromopropionyl)-5,6-epoxy-2,3-dihydro-4H,7H-10a-(benzyloxycarbonyl)quinoline

There total 5 articles about (4aR,5S,6R)-N-(3-Bromopropionyl)-5,6-epoxy-2,3-dihydro-4H,7H-10a-(benzyloxycarbonyl)quinoline 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: 42.0%

3-Bromopropionyl chloride (15486-96-1) + (4aR,5S,6R)-5,6-Epoxy-2,3,7,8-tetrahydro-4H-4a-(benzyloxycarbonyl)quinoline (171523-78-7) → (4aR,5S,6R)-N-(3-Bromopropionyl)-5,6-epoxy-2,3-dihydro-4H,7H-10a-(benzyloxycarbonyl)quinoline (171523-79-8)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; at 0 ℃; for 2.5h;

DOI:10.1021/jo00129a052

Reference yield:

(4aR,5R,6R)-5-Iodo-2,3,7,8-tetrahydro-4H-quinoline-4a,6-carbolactone (171523-75-4) → (4aR,5S,6R)-N-(3-Bromopropionyl)-5,6-epoxy-2,3-dihydro-4H,7H-10a-(benzyloxycarbonyl)quinoline (171523-79-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / n-BuLi / tetrahydrofuran / 1.) 0 deg C, 15 min., 2.) - 78 deg to r.t., overnight

2: 42 percent / NaHCO₃ / tetrahydrofuran / 2.5 h / 0 °C

With n-butyllithium; sodium hydrogencarbonate; In tetrahydrofuran;

DOI:10.1021/jo00129a052

Reference yield:

(2R,3R,4R)-1-Oxo-2-(3-azidopropyl)-3-iodocyclohexane-2,4-carbolactone (171523-74-3) → (4aR,5S,6R)-N-(3-Bromopropionyl)-5,6-epoxy-2,3-dihydro-4H,7H-10a-(benzyloxycarbonyl)quinoline (171523-79-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent / SnCl₂, NaHCO₃ / dioxane; H₂O / 1.) 7 h, room temp., 2.) 45 min.

2: 84 percent / n-BuLi / tetrahydrofuran / 1.) 0 deg C, 15 min., 2.) - 78 deg to r.t., overnight

3: 42 percent / NaHCO₃ / tetrahydrofuran / 2.5 h / 0 °C

With n-butyllithium; sodium hydrogencarbonate; tin(ll) chloride; In tetrahydrofuran; 1,4-dioxane; water;

DOI:10.1021/jo00129a052

upstream raw materials:

3-Bromopropionyl chloride

(4aR,5S,6R)-5,6-Epoxy-2,3,7,8-tetrahydro-4H-4a-(benzyloxycarbonyl)quinoline

(4aR,5R,6R)-5-Iodo-2,3,7,8-tetrahydro-4H-quinoline-4a,6-carbolactone

(2R,3R,4R)-1-Oxo-2-(3-azidopropyl)-3-iodocyclohexane-2,4-carbolactone