(3aR,8S,8aR)-6-bromo-8a-(hydroxymethyl)-5-phenyl-8-(trifluoromethyl)-3,3a,8,8a-tetrahydro-2H-furo[2,3-b]pyrrolizin-8-ol

Base Information

• Chemical Name: (3aR,8S,8aR)-6-bromo-8a-(hydroxymethyl)-5-phenyl-8-(trifluoromethyl)-3,3a,8,8a-tetrahydro-2H-furo[2,3-b]pyrrolizin-8-ol
• CAS No.: 1607459-57-3
• Molecular Formula: C₁₇H₁₅BrF₃NO₃
• Molecular Weight: 418.21
• Mol file: 1607459-57-3.mol

Synonyms:(3aR,8S,8aR)-6-bromo-8a-(hydroxymethyl)-5-phenyl-8-(trifluoromethyl)-3,3a,8,8a-tetrahydro-2H-furo[2,3-b]pyrrolizin-8-ol

Chemical Property of (3aR,8S,8aR)-6-bromo-8a-(hydroxymethyl)-5-phenyl-8-(trifluoromethyl)-3,3a,8,8a-tetrahydro-2H-furo[2,3-b]pyrrolizin-8-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,8S,8aR)-6-bromo-8a-(hydroxymethyl)-5-phenyl-8-(trifluoromethyl)-3,3a,8,8a-tetrahydro-2H-furo[2,3-b]pyrrolizin-8-ol

There total 4 articles about (3aR,8S,8aR)-6-bromo-8a-(hydroxymethyl)-5-phenyl-8-(trifluoromethyl)-3,3a,8,8a-tetrahydro-2H-furo[2,3-b]pyrrolizin-8-ol 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: 80.0%

(3aR,8S,8aR)-6-bromo-8a-(hydroxymethyl)-5-iodo-8-(trifluoromethyl)-3,3a,8,8a-tetrahydro-2H-furo[2,3-b]pyrrolizin-8-ol (1607459-53-9) + phenylboronic acid (98-80-6) → (3aR,8S,8aR)-6-bromo-8a-(hydroxymethyl)-5-phenyl-8-(trifluoromethyl)-3,3a,8,8a-tetrahydro-2H-furo[2,3-b]pyrrolizin-8-ol (1607459-57-3)

Guidance literature:

(3aR,8S,8aR)-6-bromo-8a-(hydroxymethyl)-5-iodo-8-(trifluoromethyl)-3,3a,8,8a-tetrahydro-2H-furo[2,3-b]pyrrolizin-8-ol; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; at 20 ℃; for 0.333333h; Inert atmosphere;

phenylboronic acid; With potassium carbonate; In 1,4-dioxane; water; at 80 ℃; for 4h; chemoselective reaction; Inert atmosphere;

DOI:10.1002/ejoc.201301260 DOI:10.1002/ejoc.201301260

Reference yield:

2,3-Dihydrofuran-5-carboxaldehyde (63493-93-6) → (3aR,8S,8aR)-6-bromo-8a-(hydroxymethyl)-5-phenyl-8-(trifluoromethyl)-3,3a,8,8a-tetrahydro-2H-furo[2,3-b]pyrrolizin-8-ol (1607459-57-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: (S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine; benzoic acid / toluene / 96 h / -10 °C

2.1: sodium tetrahydroborate / toluene; ethanol / 0.5 h / -10 °C

3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 0.33 h / 20 °C / Inert atmosphere

3.2: 4 h / 80 °C / Inert atmosphere

With (S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; benzoic acid; In 1,4-dioxane; ethanol; toluene; 3.1: |Suzuki Coupling / 3.2: |Suzuki Coupling;

DOI:10.1002/ejoc.201301260

Reference yield:

C6H2BrF3INO (1607459-60-8) → (3aR,8S,8aR)-6-bromo-8a-(hydroxymethyl)-5-phenyl-8-(trifluoromethyl)-3,3a,8,8a-tetrahydro-2H-furo[2,3-b]pyrrolizin-8-ol (1607459-57-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: (S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine; benzoic acid / toluene / 96 h / -10 °C

2.1: sodium tetrahydroborate / toluene; ethanol / 0.5 h / -10 °C

3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 0.33 h / 20 °C / Inert atmosphere

3.2: 4 h / 80 °C / Inert atmosphere

With (S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; benzoic acid; In 1,4-dioxane; ethanol; toluene; 3.1: |Suzuki Coupling / 3.2: |Suzuki Coupling;

DOI:10.1002/ejoc.201301260

upstream raw materials:

(3aR,8S,8aR)-6-bromo-8a-(hydroxymethyl)-5-iodo-8-(trifluoromethyl)-3,3a,8,8a-tetrahydro-2H-furo[2,3-b]pyrrolizin-8-ol

phenylboronic acid

C₆H₂BrF₃INO

2,3-Dihydrofuran-5-carboxaldehyde

Downstream raw materials:

(3aR,8S,8aR)-8a-(hydroxymethyl)-6-(4-methoxyphenyl)-5-phenyl-8-(trifluoromethyl)-3,3a,8,8a-tetrahydro-2H-furo[2,3-b]pyrrolizin-8-ol