(3S,5S)-3-amino-1,5-bis(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid

Base Information

• Chemical Name: (3S,5S)-3-amino-1,5-bis(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid
• CAS No.: 1407162-55-3
• Molecular Formula: C₁₅H₂₆N₂O₆
• Molecular Weight: 330.381
• Mol file: 1407162-55-3.mol

Synonyms:(3S,5S)-3-amino-1,5-bis(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid

Chemical Property of (3S,5S)-3-amino-1,5-bis(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5S)-3-amino-1,5-bis(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid

There total 1 articles about (3S,5S)-3-amino-1,5-bis(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid 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:

1-benzyloxycarbonyl-4-keto-L-proline (64187-47-9) → (3S,5S)-3-amino-1,5-bis(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid (1407162-55-3)

Guidance literature:

Multi-step reaction with 5 steps

1: sulfuric acid / dichloromethane / 12 h / Cooling with ice

2: water; ethanol / 72 h / Sealed tube

3: palladium on activated charcoal; hydrogen / tetrahydrofuran / 48 h

4: dmap / tetrahydrofuran / 12 h

5: potassium hydroxide / tetrahydrofuran / 3 h / Cooling with ice

With dmap; sulfuric acid; palladium on activated charcoal; hydrogen; potassium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; 2: |Bucherer-Bergs Reaction;

DOI:10.1016/j.tetlet.2016.09.032

Reference yield: 76.0%

(3S,5S)-3-amino-1,5-bis(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid (1407162-55-3) + 2,4-Dimethoxybenzaldehyde (613-45-6) → (3S,5S)-1,5-di(tert-butoxycarbonyl)-3-(2,4-dimethoxybenzylamino)pyrrolidine-3-carboxylic acid (1407162-65-5)

Guidance literature:

(3S,5S)-3-amino-1,5-bis(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid; 2,4-Dimethoxybenzaldehyde; In methanol; at 20 ℃; for 0.5h;

With sodium cyanoborohydride; In methanol; at 20 ℃; for 12h;

DOI:10.1021/ja3069648

Reference yield: 75.0%

(3S,5S)-3-amino-1,5-bis(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid (1407162-55-3) + 2-formylbenzyl allyl chloroformate (1407162-52-0) → (3S,5S)-1,5-bis[(tert-butoxy)carbonyl]-3-({[2-({[(prop-2-en-1-yloxy)carbonyl]oxy}methyl)phenyl]methyl}amino)pyrrolidine-3-carboxylic acid (1407162-62-2)

Guidance literature:

(3S,5S)-3-amino-1,5-bis(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid; 2-formylbenzyl allyl chloroformate; In methanol; at 20 ℃; for 0.5h;

With sodium cyanoborohydride; In methanol; at 20 ℃; for 12h;

DOI:10.1021/ja3069648

upstream raw materials:

1-benzyloxycarbonyl-4-keto-L-proline

Downstream raw materials:

(3'S,4S,9'S,11'S)-3-benzyl-3''-{[2-(hydroxymethyl)phenyl]methyl}-1''-(naphthalen-1-yl)-1-phenyldispiro[imidazolidine-4,5'-[1,7]diazatricyclo[7.3.0.0^3,7]dodecane-11',4''-imidazolidine]-2,2'2'',5,5'',8'-hexone

(3'S,4S,5'R,9'S)-3-{[2-(hydroxymethyl)phenyl]methyl}-1-(naphthalen-1-yl)-1''-phenyl-3''-(pyridin-3-ylmethyl)dispiro[imidazolidine-4,11'-[1,7]diazatricyclo[7.3.0.0^3,7]dodecane-5',4''-imidazolidine]-2,2'2'',5,5'',8'-hexone

(3'S,4S,5'S,9'S)-3-{[2-(hydroxymethyl)phenyl]methyl}-1-(naphthalen-1-yl)-1''-phenyl-3''-(pyridin-3-ylmethyl)dispiro[imidazolidine-4,11'-[1,7]diazatricyclo[7.3.0.0^3,7]dodecane-5',4''-imidazolidine]-2,2'2'',5,5'',8'-hexone

(3'S,4S,5'S,9'S)-3-{[2-(hydroxymethyl)phenyl]methyl}-1-(naphthalen-1-yl)-1''-phenyl-3''-(pyridin-4-ylmethyl)dispiro[imidazolidine-4,11'-[1,7]diazatricyclo[7.3.0.0^3,7]dodecane-5',4''-imidazolidine]-2,2'2'',5,5'',8'-hexone