2-[(R)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-3-oxo-pyrrolidine-1-carboxylic acid ethyl ester

Base Information

• Chemical Name: 2-[(R)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-3-oxo-pyrrolidine-1-carboxylic acid ethyl ester
• CAS No.: 142394-37-4
• Molecular Formula: C₂₁H₂₉NO₇
• Molecular Weight: 407.464
• Mol file: 142394-37-4.mol

Synonyms:

Chemical Property of 2-[(R)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-3-oxo-pyrrolidine-1-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(R)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-3-oxo-pyrrolidine-1-carboxylic acid ethyl ester

There total 3 articles about 2-[(R)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-3-oxo-pyrrolidine-1-carboxylic acid ethyl 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:

5-[((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-4-oxo-pyrrolidine-1,3-dicarboxylic acid diethyl ester → 2-[(R)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-3-oxo-pyrrolidine-1-carboxylic acid ethyl ester (142288-13-9,142394-36-3,142394-37-4,142394-38-5) + (R)-2-[(S)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-3-oxo-pyrrolidine-1-carboxylic acid ethyl ester (155975-26-1) + (S)-2-[(S)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-3-oxo-pyrrolidine-1-carboxylic acid ethyl ester (142394-38-5)

Guidance literature:

With water; sodium chloride; In dimethyl sulfoxide; at 130 ℃; Yield given. Title compound not separated from byproducts;

DOI:10.1039/c39920000166

Reference yield:

ethyl 1-ethoxycarbonyl-4-oxopyrrolidine-3-carboxylate (3751-82-4) → 2-[(R)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-3-oxo-pyrrolidine-1-carboxylic acid ethyl ester (142288-13-9,142394-36-3,142394-37-4,142394-38-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) lithium diisopropylamine (LDA), dimethylpropylene urea (DMPU) / 1.) THF, from -78 deg C to -50 deg C

2: NaCl, H₂O / dimethylsulfoxide / 130 °C

With dimethylpropylene urea; water; sodium chloride; lithium diisopropyl amide; In dimethyl sulfoxide;

DOI:10.1039/c39920000166

Reference yield:

(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde (81028-12-8) → 2-[(R)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-3-oxo-pyrrolidine-1-carboxylic acid ethyl ester (142288-13-9,142394-36-3,142394-37-4,142394-38-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) lithium diisopropylamine (LDA), dimethylpropylene urea (DMPU) / 1.) THF, from -78 deg C to -50 deg C

2: NaCl, H₂O / dimethylsulfoxide / 130 °C

With dimethylpropylene urea; water; sodium chloride; lithium diisopropyl amide; In dimethyl sulfoxide;

DOI:10.1039/c39920000166

upstream raw materials:

ethyl 1-ethoxycarbonyl-4-oxopyrrolidine-3-carboxylate

(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde