(2R,5S,6S,7S,7aR)-6,7-bis(benzyloxy)-5-butyl-1,1-difluoro-2-methylhexahydro-1H-pyrrolizine

Base Information

Chemical Name:(2R,5S,6S,7S,7aR)-6,7-bis(benzyloxy)-5-butyl-1,1-difluoro-2-methylhexahydro-1H-pyrrolizine
CAS No.:1401240-81-0
Molecular Formula:C₂₆H₃₃F₂NO₂
Molecular Weight:429.55
Hs Code.:

Synonyms:(2R,5S,6S,7S,7aR)-6,7-bis(benzyloxy)-5-butyl-1,1-difluoro-2-methylhexahydro-1H-pyrrolizine

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Chemical Property of (2R,5S,6S,7S,7aR)-6,7-bis(benzyloxy)-5-butyl-1,1-difluoro-2-methylhexahydro-1H-pyrrolizine

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Technology Process of (2R,5S,6S,7S,7aR)-6,7-bis(benzyloxy)-5-butyl-1,1-difluoro-2-methylhexahydro-1H-pyrrolizine

There total 20 articles about (2R,5S,6S,7S,7aR)-6,7-bis(benzyloxy)-5-butyl-1,1-difluoro-2-methylhexahydro-1H-pyrrolizine 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: 58.0%

: 1401240-75-2
(1S,2R,6R,7aR)-1,2-bis(benzyloxy)-7,7-difluoro-6-methyltetrahydro-1H-pyrrolizin-3(2H)-one

: 693-04-9
butyl magnesium bromide

: 1401240-81-0
(2R,5S,6S,7S,7aR)-6,7-bis(benzyloxy)-5-butyl-1,1-difluoro-2-methylhexahydro-1H-pyrrolizine

Guidance literature:: (1S,2R,6R,7aR)-1,2-bis(benzyloxy)-7,7-difluoro-6-methyltetrahydro-1H-pyrrolizin-3(2H)-one; butyl magnesium bromide; In tetrahydrofuran;

With hydrogenchloride; In water;

With sodium cyanoborohydride;
DOI:10.1021/jo301327s

Reference yield: 15.0%

: 109-72-8,29786-93-4
n-butyllithium

: 1401240-75-2
(1S,2R,6R,7aR)-1,2-bis(benzyloxy)-7,7-difluoro-6-methyltetrahydro-1H-pyrrolizin-3(2H)-one

: 1401240-81-0
(2R,5S,6S,7S,7aR)-6,7-bis(benzyloxy)-5-butyl-1,1-difluoro-2-methylhexahydro-1H-pyrrolizine

: 1401240-83-2
(S)-6-(benzyloxy)-1-butyl-2-methyl-2H-pyrrolizin-5(3H)-one

Guidance literature:: n-butyllithium; With cerium(III) chloride; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

(1S,2R,6R,7aR)-1,2-bis(benzyloxy)-7,7-difluoro-6-methyltetrahydro-1H-pyrrolizin-3(2H)-one; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

With sodium cyanoborohydride; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; at 0 ℃; for 1h;
DOI:10.1021/jo301327s

Reference yield:

: 138794-81-7
(2R,3R)-2,3-bis(benzyloxy)tartaric acid

: 1401240-81-0
(2R,5S,6S,7S,7aR)-6,7-bis(benzyloxy)-5-butyl-1,1-difluoro-2-methylhexahydro-1H-pyrrolizine

Guidance literature:: Multi-step reaction with 9 steps

1: acetyl chloride / 4 h / Reflux

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

3: acetyl chloride / 5 h / Reflux

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

5: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 16 h / 0 - 20 °C

6: tetrabutylammonium triphenyldifluorosilicate / N,N-dimethyl-formamide / 8 h / -78 °C

7: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 1 h / Inert atmosphere; Reflux

8: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 48 h / 20 °C / Inert atmosphere

9: tetrahydrofuran

With triethylsilane; ammonium cerium (IV) nitrate; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; acetyl chloride; triphenylphosphine; tetrabutylammonium triphenyldifluorosilicate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/jo301327s