(1S,2S,3S,7S,8aR)-1,2-bis(benzyloxy)-3-ethyl-8,8-difluoro-7-methyloctahydroindolizine

Base Information

• Chemical Name: (1S,2S,3S,7S,8aR)-1,2-bis(benzyloxy)-3-ethyl-8,8-difluoro-7-methyloctahydroindolizine
• CAS No.: 1401240-89-8
• Molecular Formula: C₂₅H₃₁F₂NO₂
• Molecular Weight: 415.523
• Mol file: 1401240-89-8.mol

Synonyms:

Chemical Property of (1S,2S,3S,7S,8aR)-1,2-bis(benzyloxy)-3-ethyl-8,8-difluoro-7-methyloctahydroindolizine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3S,7S,8aR)-1,2-bis(benzyloxy)-3-ethyl-8,8-difluoro-7-methyloctahydroindolizine

There total 10 articles about (1S,2S,3S,7S,8aR)-1,2-bis(benzyloxy)-3-ethyl-8,8-difluoro-7-methyloctahydroindolizine 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: 50.0%

(1S,2R,7S,8aR)-1,2-bis(benzyloxy)-8,8-difluoro-7-methylhexahydro-indolizin-3(5H)-one (1401240-85-4) + ethylmagnesium chloride (2386-64-3) → (1S,2S,3R,7S,8aR)-1,2-bis(benzyloxy)-3-ethyl-8,8-difluoro-7-methyloctahydroindolizine (1401240-87-6) + (1S,2S,3S,7S,8aR)-1,2-bis(benzyloxy)-3-ethyl-8,8-difluoro-7-methyloctahydroindolizine (1401240-89-8)

Guidance literature:

(1S,2R,7S,8aR)-1,2-bis(benzyloxy)-8,8-difluoro-7-methylhexahydro-indolizin-3(5H)-one; ethylmagnesium chloride; In tetrahydrofuran;

With hydrogenchloride; In water;

With sodium cyanoborohydride;

DOI:10.1021/jo301327s

Reference yield:

diethyl (2R,3R)-2,3-bis(benzyloxy)butane-1,4-dioate (77312-71-1) → (1S,2S,3R,7S,8aR)-1,2-bis(benzyloxy)-3-ethyl-8,8-difluoro-7-methyloctahydroindolizine (1401240-87-6) + (1S,2S,3S,7S,8aR)-1,2-bis(benzyloxy)-3-ethyl-8,8-difluoro-7-methyloctahydroindolizine (1401240-89-8)

Guidance literature:

Multi-step reaction with 10 steps

1: lithium hydroxide monohydrate; water / ethanol / 24 h / 0 °C

2: acetyl chloride / 4 h / Reflux

3: dichloromethane / 5 h / 0 °C / Reflux

4: acetyl chloride / 5 h / Reflux

5: ammonium cerium (IV) nitrate / water; acetonitrile / 4 h / 0 - 20 °C

6: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran

7: tetrabutylammonium triphenyldifluorosilicate / N,N-dimethyl-formamide / 10 h / -78 °C

8: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 1 h / Inert atmosphere; Reflux

9: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 24 h / Reflux

10: tetrahydrofuran

With triethylsilane; ammonium cerium (IV) nitrate; lithium hydroxide monohydrate; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; boron trifluoride diethyl etherate; water; tri-n-butyl-tin hydride; acetyl chloride; triphenylphosphine; tetrabutylammonium triphenyldifluorosilicate; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/jo301327s

Reference yield:

(3R,4R)-3,4-bis(benzyloxy)-1-(4-methoxybenzyl)-pyrrolidine-2,5-dione (321566-90-9) → (1S,2S,3R,7S,8aR)-1,2-bis(benzyloxy)-3-ethyl-8,8-difluoro-7-methyloctahydroindolizine (1401240-87-6) + (1S,2S,3S,7S,8aR)-1,2-bis(benzyloxy)-3-ethyl-8,8-difluoro-7-methyloctahydroindolizine (1401240-89-8)

Guidance literature:

Multi-step reaction with 6 steps

1: ammonium cerium (IV) nitrate / water; acetonitrile / 4 h / 0 - 20 °C

2: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran

3: tetrabutylammonium triphenyldifluorosilicate / N,N-dimethyl-formamide / 10 h / -78 °C

4: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 1 h / Inert atmosphere; Reflux

5: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 24 h / Reflux

6: tetrahydrofuran

With triethylsilane; ammonium cerium (IV) nitrate; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; triphenylphosphine; tetrabutylammonium triphenyldifluorosilicate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/jo301327s

upstream raw materials:

diethyl (2R,3R)-2,3-bis(benzyloxy)butane-1,4-dioate

(2R,3R)-2,3-bis(benzyloxy)tartaric acid

(3R,4R)-3,4-bis(benzyloxy)-3,4-dihydro-2,5-furandione

(3R,4R)-3,4-bis(benzyloxy)-1-(4-methoxybenzyl)-pyrrolidine-2,5-dione