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

Base Information

• Chemical Name: (1S,2R,6R,7aR)-1,2-bis(benzyloxy)-7,7-difluoro-6-methyltetrahydro-1H-pyrrolizin-3(2H)-one
• CAS No.: 1401240-75-2
• Molecular Formula: C₂₂H₂₃F₂NO₃
• Molecular Weight: 387.426
• Mol file: 1401240-75-2.mol

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

Chemical Property of (1S,2R,6R,7aR)-1,2-bis(benzyloxy)-7,7-difluoro-6-methyltetrahydro-1H-pyrrolizin-3(2H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,6R,7aR)-1,2-bis(benzyloxy)-7,7-difluoro-6-methyltetrahydro-1H-pyrrolizin-3(2H)-one

There total 9 articles about (1S,2R,6R,7aR)-1,2-bis(benzyloxy)-7,7-difluoro-6-methyltetrahydro-1H-pyrrolizin-3(2H)-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: 73.0%

(1R,2R,6R,7aR)-1,2-bis(benzyloxy)-7,7-difluoro-7a-hydroxy-6-methyltetrahydro-1H-pyrrolizin-3(2H)-one (1401240-59-2) → (1S,2R,6R,7aR)-1,2-bis(benzyloxy)-7,7-difluoro-6-methyltetrahydro-1H-pyrrolizin-3(2H)-one (1401240-75-2)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 48h; Inert atmosphere;

DOI:10.1021/jo301327s

Reference yield:

(3R,4R)-3,4-bis(benzyloxy)-3,4-dihydro-2,5-furandione (97506-01-9) → (1S,2R,6R,7aR)-1,2-bis(benzyloxy)-7,7-difluoro-6-methyltetrahydro-1H-pyrrolizin-3(2H)-one (1401240-75-2)

Guidance literature:

Multi-step reaction with 7 steps

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

2: acetyl chloride / 5 h / Reflux

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

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

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

6: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 1 h / Inert atmosphere; Reflux

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

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

Reference yield:

(2R,3R)-2,3-bis(benzyloxy)tartaric acid (138794-81-7) → (1S,2R,6R,7aR)-1,2-bis(benzyloxy)-7,7-difluoro-6-methyltetrahydro-1H-pyrrolizin-3(2H)-one (1401240-75-2)

Guidance literature:

Multi-step reaction with 8 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

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

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

Downstream raw materials:

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

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

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

(2R,5S,6S,7S,7aR)-6,7-bis(benzyloxy)-1,1-difluoro-5-isopropyl-2-methyl-hexahydro-1H-pyrrolizine