(2S,3R)-3-Isopropyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

Base Information

• Chemical Name: (2S,3R)-3-Isopropyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester
• CAS No.: 745016-00-6
• Molecular Formula: C₂₀H₂₉NO₄
• Molecular Weight: 347.455
• Mol file: 745016-00-6.mol

Synonyms:

Chemical Property of (2S,3R)-3-Isopropyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-3-Isopropyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

There total 5 articles about (2S,3R)-3-Isopropyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl 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:

(S)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate (81658-27-7) → (2S,3R)-3-Isopropyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester (745016-00-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: copper bromide dimethylsulfide complex / diethyl ether / -20 °C

1.2: 73 percent / trimethylsilyl chloride / diethyl ether / -78 °C

2.1: 92 percent / H₂ / Pd/C / ethanol / 760 Torr

3.1: HCl / ethyl acetate / -20 °C

4.1: LAH / tetrahydrofuran / Heating

5.1: aq. K₂CO₃ / tetrahydrofuran

6.1: acetone; Jones reagent

7.1: H₂SO₄ / CH₂Cl₂

With hydrogenchloride; lithium aluminium tetrahydride; jones reagent; copper(I) bromide dimethylsulfide complex; sulfuric acid; hydrogen; potassium carbonate; acetone; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; ethyl acetate; 6.1: Jones oxidation;

DOI:10.1016/j.bmcl.2004.01.078

Reference yield:

(2S,3R)-N-tert-butoxycarbonyl-2-(tert-butyldimethylsilyloxymethyl)-3-(iso-propenyl)-pyrrolidine-5-one (745013-95-0) → (2S,3R)-3-Isopropyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester (745016-00-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 92 percent / H₂ / Pd/C / ethanol / 760 Torr

2: HCl / ethyl acetate / -20 °C

3: LAH / tetrahydrofuran / Heating

4: aq. K₂CO₃ / tetrahydrofuran

5: acetone; Jones reagent

6: H₂SO₄ / CH₂Cl₂

With hydrogenchloride; lithium aluminium tetrahydride; jones reagent; sulfuric acid; hydrogen; potassium carbonate; acetone; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; 5: Jones oxidation;

DOI:10.1016/j.bmcl.2004.01.078

Reference yield:

((2S,3R)-3-Isopropyl-pyrrolidin-2-yl)-methanol (696645-67-7) → (2S,3R)-3-Isopropyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester (745016-00-6)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. K₂CO₃ / tetrahydrofuran

2: acetone; Jones reagent

3: H₂SO₄ / CH₂Cl₂

With jones reagent; sulfuric acid; potassium carbonate; acetone; In tetrahydrofuran; dichloromethane; 2: Jones oxidation;

DOI:10.1016/j.bmcl.2004.01.078

upstream raw materials:

isobutene

(2S,3R)-3-Isopropyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

(S)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate

((2S,3R)-3-Isopropyl-pyrrolidin-2-yl)-methanol