5-Oxo-6,7-dihydro-5H-pyrrolizine-3-carboxylic acid 4-methoxy-benzyl ester

Base Information

• Chemical Name: 5-Oxo-6,7-dihydro-5H-pyrrolizine-3-carboxylic acid 4-methoxy-benzyl ester
• CAS No.: 132114-54-6
• Molecular Formula: C₁₆H₁₅NO₄
• Molecular Weight: 285.299

Synonyms:5-Oxo-6,7-dihydro-5H-pyrrolizine-3-carboxylic acid 4-methoxy-benzyl ester

Chemical Property of 5-Oxo-6,7-dihydro-5H-pyrrolizine-3-carboxylic acid 4-methoxy-benzyl ester

Chemical Property:

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Technology Process of 5-Oxo-6,7-dihydro-5H-pyrrolizine-3-carboxylic acid 4-methoxy-benzyl ester

There total 8 articles about 5-Oxo-6,7-dihydro-5H-pyrrolizine-3-carboxylic acid 4-methoxy-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: 35.0%

(1S,7aR)-1-Hydroxy-5-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carboxylic acid 4-methoxy-benzyl ester (132114-48-8) → 5-Oxo-6,7-dihydro-5H-pyrrolizine-3-carboxylic acid 4-methoxy-benzyl ester (132114-54-6)

Guidance literature:

With oxalyl dichloride; triethylamine; In dimethyl sulfoxide; at -40 ℃;

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

Reference yield:

p-Anisaldehyde dimethyl acetal (2186-92-7) → 5-Oxo-6,7-dihydro-5H-pyrrolizine-3-carboxylic acid 4-methoxy-benzyl ester (132114-54-6)

Guidance literature:

Multi-step reaction with 7 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 / 4 h / Ambient temperature

6: sodium hydroxide / 1,4-dioxane; water / 0.08 h / 5 °C

7: oxalyl dichloride; triethylamine / dimethyl sulfoxide / -40 °C

With dmap; sodium hydroxide; oxalyl dichloride; dimethylsulfide; boron trifluoride diethyl etherate; dansylcadaverine; ozone; triethylamine; In tetrahydrofuran; 1,4-dioxane; water; dimethyl sulfoxide;

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

Reference yield:

5(S)-Vinyl-2-Pyrrolidinone (7529-16-0) → 5-Oxo-6,7-dihydro-5H-pyrrolizine-3-carboxylic acid 4-methoxy-benzyl ester (132114-54-6)

Guidance literature:

Multi-step reaction with 7 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 / 4 h / Ambient temperature

6: sodium hydroxide / 1,4-dioxane; water / 0.08 h / 5 °C

7: oxalyl dichloride; triethylamine / dimethyl sulfoxide / -40 °C

With dmap; sodium hydroxide; oxalyl dichloride; dimethylsulfide; boron trifluoride diethyl etherate; dansylcadaverine; ozone; triethylamine; In tetrahydrofuran; 1,4-dioxane; water; dimethyl sulfoxide;

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

upstream raw materials:

(1S,7aR)-1-Hydroxy-5-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carboxylic acid 4-methoxy-benzyl ester

p-Anisaldehyde dimethyl acetal

5(S)-Vinyl-2-Pyrrolidinone

1-[Methoxy-(4-methoxy-phenyl)-methyl]-5-oxo-pyrrolidine-2-carbaldehyde

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