Technology Process of (2R,5S,6S,7S,7aR)-6,7-bis(benzyloxy)-5-ethyl-1,1-difluoro-2-methylhexahydro-1H-pyrrolizine
There total 10 articles about (2R,5S,6S,7S,7aR)-6,7-bis(benzyloxy)-5-ethyl-1,1-difluoro-2-methylhexahydro-1H-pyrrolizine which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(1S,2R,6R,7aR)-1,2-bis(benzyloxy)-7,7-difluoro-6-methyltetrahydro-1H-pyrrolizin-3(2H)-one; ethylmagnesium chloride;
In
tetrahydrofuran;
at 0 ℃;
for 0.5h;
With
hydrogenchloride;
In
tetrahydrofuran; 1,4-dioxane; methanol;
With
sodium cyanoborohydride;
In
tetrahydrofuran; 1,4-dioxane; methanol;
for 1h;
DOI:10.1021/jo301327s
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: acetyl chloride / 4 h / Reflux
2.1: dichloromethane / 5 h / 0 °C / Reflux
3.1: acetyl chloride / 5 h / Reflux
4.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4 h / 0 - 20 °C
5.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 16 h / 0 - 20 °C
6.1: tetrabutylammonium triphenyldifluorosilicate / N,N-dimethyl-formamide / 8 h / -78 °C
7.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 1 h / Inert atmosphere; Reflux
8.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 48 h / 20 °C / Inert atmosphere
9.1: tetrahydrofuran / 0.5 h / 0 °C
9.3: 1 h
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
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: dichloromethane / 5 h / 0 °C / Reflux
2.1: acetyl chloride / 5 h / Reflux
3.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4 h / 0 - 20 °C
4.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 16 h / 0 - 20 °C
5.1: tetrabutylammonium triphenyldifluorosilicate / N,N-dimethyl-formamide / 8 h / -78 °C
6.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 1 h / Inert atmosphere; Reflux
7.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 48 h / 20 °C / Inert atmosphere
8.1: tetrahydrofuran / 0.5 h / 0 °C
8.3: 1 h
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
