(1R,7aR)-1-Acetoxy-2-(diphenyl-phosphinoyloxy)-5-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carboxylic acid 4-nitro-benzyl ester

Base Information

• Chemical Name: (1R,7aR)-1-Acetoxy-2-(diphenyl-phosphinoyloxy)-5-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carboxylic acid 4-nitro-benzyl ester
• CAS No.: 132114-52-4
• Molecular Formula: C₂₉H₂₅N₂O₉P
• Molecular Weight: 576.499
• Mol file: 132114-52-4.mol

Synonyms:

Chemical Property of (1R,7aR)-1-Acetoxy-2-(diphenyl-phosphinoyloxy)-5-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carboxylic acid 4-nitro-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,7aR)-1-Acetoxy-2-(diphenyl-phosphinoyloxy)-5-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carboxylic acid 4-nitro-benzyl ester

There total 11 articles about (1R,7aR)-1-Acetoxy-2-(diphenyl-phosphinoyloxy)-5-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carboxylic acid 4-nitro-benzyl ester 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:

(1R,7aR)-1-Acetoxy-2,5-dioxo-hexahydro-pyrrolizine-3-carboxylic acid 4-nitro-benzyl ester (132114-51-3) + Diphenylphosphinic chloride (1499-21-4) → (1R,7aR)-1-Acetoxy-2-(diphenyl-phosphinoyloxy)-5-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carboxylic acid 4-nitro-benzyl ester (132114-52-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 5 ℃;

DOI:10.1016/S0040-4039(00)97208-3

Reference yield:

5(S)-Vinyl-2-Pyrrolidinone (7529-16-0) → (1R,7aR)-1-Acetoxy-2-(diphenyl-phosphinoyloxy)-5-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carboxylic acid 4-nitro-benzyl ester (132114-52-4)

Guidance literature:

Multi-step reaction with 10 steps

1: boron trifluoride diethyl etherate / 1 h / Ambient temperature

2: dimethylsulfide; dansylcadaverine; ozone / 1) MeOH, 78 deg C

3: tetrahydrofuran / 16 h / Ambient temperature

4: dmap; dansylcadaverine; triethylamine

5: sulfur dioxide / tetrahydrofuran

8: potassium carbonate / N,N-dimethyl-formamide

9: pyridine; 1,2-Dichloro-3-iodobenzene / benzene

10: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 °C

With pyridine; dmap; dimethylsulfide; 1,2-Dichloro-3-iodobenzene; boron trifluoride diethyl etherate; dansylcadaverine; sulfur dioxide; potassium carbonate; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1016/S0040-4039(00)97208-3

Reference yield:

Acetic acid 1-(5-oxo-pyrrolidin-2-yl)-allyl ester (132114-40-0) → (1R,7aR)-1-Acetoxy-2-(diphenyl-phosphinoyloxy)-5-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carboxylic acid 4-nitro-benzyl ester (132114-52-4)

Guidance literature:

Multi-step reaction with 5 steps

3: potassium carbonate / N,N-dimethyl-formamide

4: pyridine; 1,2-Dichloro-3-iodobenzene / benzene

5: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 °C

With pyridine; 1,2-Dichloro-3-iodobenzene; potassium carbonate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1016/S0040-4039(00)97208-3

upstream raw materials:

(1R,7aR)-1-Acetoxy-2,5-dioxo-hexahydro-pyrrolizine-3-carboxylic acid 4-nitro-benzyl ester

Diphenylphosphinic chloride

5(S)-Vinyl-2-Pyrrolidinone

Acetic acid 1-(5-oxo-pyrrolidin-2-yl)-allyl ester

Downstream raw materials:

(1R,7aR)-1-Acetoxy-2-ethylsulfanyl-5-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carboxylic acid 4-nitro-benzyl ester