(1S,2R,5R,8R,8aR)-5-[2'-oxo-2'-(4-bromophenyl)ethyl]-1,2,8-trihydroxy-indolizidine

Base Information

• Chemical Name: (1S,2R,5R,8R,8aR)-5-[2'-oxo-2'-(4-bromophenyl)ethyl]-1,2,8-trihydroxy-indolizidine
• CAS No.: 675624-08-5
• Molecular Formula: C₁₆H₂₀BrNO₄
• Molecular Weight: 370.243
• Mol file: 675624-08-5.mol

Synonyms:(1S,2R,5R,8R,8aR)-5-[2'-oxo-2'-(4-bromophenyl)ethyl]-1,2,8-trihydroxy-indolizidine

Chemical Property of (1S,2R,5R,8R,8aR)-5-[2'-oxo-2'-(4-bromophenyl)ethyl]-1,2,8-trihydroxy-indolizidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,5R,8R,8aR)-5-[2'-oxo-2'-(4-bromophenyl)ethyl]-1,2,8-trihydroxy-indolizidine

There total 4 articles about (1S,2R,5R,8R,8aR)-5-[2'-oxo-2'-(4-bromophenyl)ethyl]-1,2,8-trihydroxy-indolizidine 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: 29.0%

para-bromoacetophenone (99-90-1) + (3R,4S,5R)-3,4-(isopropylidenedioxy)-5-[(5'R)-2'-methoxytetrahydrofuran-5'-yl]pyrrolidine → (1S,2R,5R,8R,8aR)-5-[2'-oxo-2'-(4-bromophenyl)ethyl]-1,2,8-trihydroxy-indolizidine (675624-08-5) + (1S,2R,5S,8R,8aR)-5-[(1'S,2'R,8'R,8'aR)-1',2',8'-trihydroxy-1',2',3',7',8',8a'-hexahydro-6'-indolizinyl]-1,2,8-trihydroxy-indolizidine

Guidance literature:

With hydrogenchloride; In ethanol; for 3h; Heating;

DOI:10.1021/ol049947m

Reference yield:

(5R)-5-[(1'S,2'R,3'R)-4'-azido-2',3'(isopropylidenedioxy)-1'-(methanesulfonyloxy)butyl]tetrahydrofuran-2-one (182355-67-5) → (1S,2R,5R,8R,8aR)-5-[2'-oxo-2'-(4-bromophenyl)ethyl]-1,2,8-trihydroxy-indolizidine (675624-08-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 100 percent / diisobutylaluminum hydride / CH₂Cl₂ / 3 h / -78 °C

2.1: 100 percent / aq. HCl / 20 °C

3.1: H₂ / Pd(OH)2/C / methanol / 3 h

3.2: 84 percent / Et₃N / methanol / 4 h / 60 °C

4.1: 29 percent / HCl / ethanol / 3 h / Heating

With hydrogenchloride; hydrogen; diisobutylaluminium hydride; palladium dihydroxide; In methanol; ethanol; dichloromethane; 4.1: Mannich reaction;

DOI:10.1021/ol049947m

Reference yield:

Methanesulfonic acid (S)-((4R,5R)-5-azidomethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-((R)-5-hydroxy-tetrahydro-furan-2-yl)-methyl ester → (1S,2R,5R,8R,8aR)-5-[2'-oxo-2'-(4-bromophenyl)ethyl]-1,2,8-trihydroxy-indolizidine (675624-08-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 100 percent / aq. HCl / 20 °C

2.1: H₂ / Pd(OH)2/C / methanol / 3 h

2.2: 84 percent / Et₃N / methanol / 4 h / 60 °C

3.1: 29 percent / HCl / ethanol / 3 h / Heating

With hydrogenchloride; hydrogen; palladium dihydroxide; In methanol; ethanol; 3.1: Mannich reaction;

DOI:10.1021/ol049947m

upstream raw materials:

para-bromoacetophenone

(5R)-5-[(1'S,2'R,3'R)-4'-azido-2',3'(isopropylidenedioxy)-1'-(methanesulfonyloxy)butyl]tetrahydrofuran-2-one