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

Base Information

Chemical Name:(1S,2R,7S,8aR)-1,2-bis(benzyloxy)-8,8-difluoro-7-methylhexahydro-indolizin-3(5H)-one
CAS No.:1401240-85-4
Molecular Formula:C₂₃H₂₅F₂NO₃
Molecular Weight:401.453
Hs Code.:

Synonyms:

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Chemical Property of (1S,2R,7S,8aR)-1,2-bis(benzyloxy)-8,8-difluoro-7-methylhexahydro-indolizin-3(5H)-one

Chemical Property:

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Technology Process of (1S,2R,7S,8aR)-1,2-bis(benzyloxy)-8,8-difluoro-7-methylhexahydro-indolizin-3(5H)-one

There total 9 articles about (1S,2R,7S,8aR)-1,2-bis(benzyloxy)-8,8-difluoro-7-methylhexahydro-indolizin-3(5H)-one 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: 40.0%

: 1401240-65-0
(1R,2R,7R,8aR)-1,2-bis(benzyloxy)-8,8-difluoro-8a-hydroxy-7-methylhexahydroindolizin-3(5H)-one

: 1401240-85-4
(1S,2R,7S,8aR)-1,2-bis(benzyloxy)-8,8-difluoro-7-methylhexahydro-indolizin-3(5H)-one

: 1401240-86-5
(1S,2R,7S,8aS)-1,2-bis(benzyloxy)-8,8-difluoro-7-methylhexahydro-indolizin-3(5H)-one

Guidance literature:: With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; for 24h; Reflux;
DOI:10.1021/jo301327s

Reference yield:

: 321566-90-9
(3R,4R)-3,4-bis(benzyloxy)-1-(4-methoxybenzyl)-pyrrolidine-2,5-dione

: 1401240-85-4
(1S,2R,7S,8aR)-1,2-bis(benzyloxy)-8,8-difluoro-7-methylhexahydro-indolizin-3(5H)-one

: 1401240-86-5
(1S,2R,7S,8aS)-1,2-bis(benzyloxy)-8,8-difluoro-7-methylhexahydro-indolizin-3(5H)-one

Guidance literature:: Multi-step reaction with 5 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

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

Reference yield:

: 77312-71-1
diethyl (2R,3R)-2,3-bis(benzyloxy)butane-1,4-dioate

: 1401240-85-4
(1S,2R,7S,8aR)-1,2-bis(benzyloxy)-8,8-difluoro-7-methylhexahydro-indolizin-3(5H)-one

: 1401240-86-5
(1S,2R,7S,8aS)-1,2-bis(benzyloxy)-8,8-difluoro-7-methylhexahydro-indolizin-3(5H)-one

Guidance literature:: Multi-step reaction with 9 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

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