(2S,3S)-2-(3-amino-3-benzyl-2-oxo-pyrrolidin-1-yl)-propionic acid methyl ester

Base Information

• Chemical Name: (2S,3S)-2-(3-amino-3-benzyl-2-oxo-pyrrolidin-1-yl)-propionic acid methyl ester
• CAS No.: 220569-39-1
• Molecular Formula: C₁₅H₂₀N₂O₃
• Molecular Weight: 276.335
• Mol file: 220569-39-1.mol

Synonyms:(2S,3S)-2-(3-amino-3-benzyl-2-oxo-pyrrolidin-1-yl)-propionic acid methyl ester

Chemical Property of (2S,3S)-2-(3-amino-3-benzyl-2-oxo-pyrrolidin-1-yl)-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-2-(3-amino-3-benzyl-2-oxo-pyrrolidin-1-yl)-propionic acid methyl ester

There total 5 articles about (2S,3S)-2-(3-amino-3-benzyl-2-oxo-pyrrolidin-1-yl)-propionic acid methyl 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: 90.0%

(2S,3S)-2-(3-benzyl-3-benzyloxycarbonylamino-2-oxo-pyrrolidin-1-yl)-propionic acid methyl ester (117162-07-9) → (2S,3S)-2-(3-amino-3-benzyl-2-oxo-pyrrolidin-1-yl)-propionic acid methyl ester (220569-39-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 17h;

DOI:10.1016/S0968-0896(98)80022-9

Reference yield:

(2S,4S)-4-benzyl-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid benzyl ester (191980-50-4) → (2S,3S)-2-(3-amino-3-benzyl-2-oxo-pyrrolidin-1-yl)-propionic acid methyl ester (220569-39-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.5 h / -78 °C

1.2: 77 percent / tetrahydrofuran; toluene / 16 h / -78 - 25 °C

2.1: ozone; NaHCO₃ / CH₂Cl₂; methanol / -78 °C

2.2: 95 percent / Me₂S / CH₂Cl₂; methanol / -78 - 25 °C

3.1: NaOAc; 4 Angstroem molecular sieves; NaCNBH₃ / methanol / 25 °C

4.1: 610 mg / 1-hydroxybenzotriazole / toluene / 16 h / Heating

5.1: 90 percent / hydrogen / Pd/C / ethanol / 17 h

With 4 A molecular sieve; hydrogen; sodium acetate; potassium hexamethylsilazane; sodium cyanoborohydride; sodium hydrogencarbonate; benzotriazol-1-ol; ozone; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; toluene; 1.1: Metallation / 1.2: Alkylation / 2.1: ozonolysis / 2.2: Reduction / 3.1: Alkylation / 4.1: Cyclization / 5.1: Hydrogenolysis;

DOI:10.1016/S0968-0896(98)80022-9

Reference yield:

(2S,4R)-4-benzyl-2-tert-butyl-5-oxo-4-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid benzyl ester (220569-30-2) → (2S,3S)-2-(3-amino-3-benzyl-2-oxo-pyrrolidin-1-yl)-propionic acid methyl ester (220569-39-1)

Guidance literature:

Multi-step reaction with 3 steps

1: NaOAc; 4 Angstroem molecular sieves; NaCNBH₃ / methanol / 25 °C

2: 610 mg / 1-hydroxybenzotriazole / toluene / 16 h / Heating

3: 90 percent / hydrogen / Pd/C / ethanol / 17 h

With 4 A molecular sieve; hydrogen; sodium acetate; sodium cyanoborohydride; benzotriazol-1-ol; palladium on activated charcoal; In methanol; ethanol; toluene; 1: Alkylation / 2: Cyclization / 3: Hydrogenolysis;

DOI:10.1016/S0968-0896(98)80022-9

upstream raw materials:

(2S,3S)-2-(3-benzyl-3-benzyloxycarbonylamino-2-oxo-pyrrolidin-1-yl)-propionic acid methyl ester

(2S,4S)-4-benzyl-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid benzyl ester

(2S,4R)-4-benzyl-2-tert-butyl-5-oxo-4-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid benzyl ester

(2S,4S)-4-allyl-4-benzyl-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid benzyl ester

Downstream raw materials:

(2S,3S)-2-(3-benzenesulfonylamino-3-benzyl-2-oxo-pyrrolidin-1-yl)-propionic acid methyl ester

(2S,3S)-N-[3-benzyl-1-(2-hydroxyl-1-methyl-ethyl)-2-oxo-pyrrolidin-3-yl]-methane-sulfonamide

(2S,3S)-N-[3-benzyl-1-(2-hydroxyl-1-methyl-ethyl)-2-oxo-pyrrolidin-3-yl]-benzene-sulfonamide

(2S,3S)-2-(3-benzyl-3-methylsulfonylamino-2-oxo-pyrrolidin-1-yl)-propionic acid methyl ester