(2S,3R)-N-tert-butoxycarbonyl-2-(tert-butyldimethylsilyloxymethyl)-3-(iso-propenyl)-pyrrolidine-5-one

Base Information

• Chemical Name: (2S,3R)-N-tert-butoxycarbonyl-2-(tert-butyldimethylsilyloxymethyl)-3-(iso-propenyl)-pyrrolidine-5-one
• CAS No.: 745013-95-0
• Molecular Formula: C₁₉H₃₅NO₄Si
• Molecular Weight: 369.577
• Mol file: 745013-95-0.mol

Synonyms:(2S,3R)-N-tert-butoxycarbonyl-2-(tert-butyldimethylsilyloxymethyl)-3-(iso-propenyl)-pyrrolidine-5-one

Chemical Property of (2S,3R)-N-tert-butoxycarbonyl-2-(tert-butyldimethylsilyloxymethyl)-3-(iso-propenyl)-pyrrolidine-5-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-N-tert-butoxycarbonyl-2-(tert-butyldimethylsilyloxymethyl)-3-(iso-propenyl)-pyrrolidine-5-one

There total 1 articles about (2S,3R)-N-tert-butoxycarbonyl-2-(tert-butyldimethylsilyloxymethyl)-3-(iso-propenyl)-pyrrolidine-5-one 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)-Pyroglutaminol (17342-08-4) → (2S,3R)-N-tert-butoxycarbonyl-2-(tert-butyldimethylsilyloxymethyl)-3-(iso-propenyl)-pyrrolidine-5-one (745013-95-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine / dichloromethane

2.1: dmap; triethylamine / dichloromethane

3.1: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C

3.3: 0 - 20 °C

4.1: tert.-butyl lithium / tetrahydrofuran; pentane / 0.25 h / -78 °C

4.2: 1 h / -50 °C

With dmap; tert.-butyl lithium; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; pentane;

DOI:10.1002/cmdc.201000543

Reference yield:

(2S,3R)-N-tert-butoxycarbonyl-2-(tert-butyldimethylsilyloxymethyl)-3-(iso-propenyl)-pyrrolidine-5-one (745013-95-0) → (2S,3R)-2-Hydroxymethyl-3-isopropyl-pyrrolidine-1-carboxylic acid benzyl ester (745014-69-1)

Guidance literature:

Multi-step reaction with 4 steps

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

2: HCl / ethyl acetate / -20 °C

3: LAH / tetrahydrofuran / Heating

4: aq. K₂CO₃ / tetrahydrofuran

With hydrogenchloride; lithium aluminium tetrahydride; hydrogen; potassium carbonate; palladium on activated charcoal; In tetrahydrofuran; ethanol; ethyl acetate;

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 (745015-84-3)

Guidance literature:

Multi-step reaction with 5 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

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

DOI:10.1016/j.bmcl.2004.01.078

upstream raw materials:

(S)-Pyroglutaminol

Downstream raw materials:

(4R,5S)-5-Hydroxymethyl-4-isopropyl-pyrrolidin-2-one

(2S,3R)-2-Hydroxymethyl-3-isopropyl-pyrrolidine-1-carboxylic acid benzyl ester

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

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