1,2-Pyrrolidinedicarboxylic acid, 5-hydroxy-, 1-(1,1-diMethylethyl) 2-ethyl ester, (2S)-

Base Information

• Chemical Name: 1,2-Pyrrolidinedicarboxylic acid, 5-hydroxy-, 1-(1,1-diMethylethyl) 2-ethyl ester, (2S)-
• CAS No.: 194594-23-5
• Molecular Formula: C12H21NO5
• Molecular Weight: 259.302
• Hs Code.: 2933990090
• Mol file: 194594-23-5.mol

Synonyms:(2S)-1-tert-Butyl 2-ethyl 5-hydroxypyrrolidine-1,2-dicarboxylate;

Chemical Property of 1,2-Pyrrolidinedicarboxylic acid, 5-hydroxy-, 1-(1,1-diMethylethyl) 2-ethyl ester, (2S)-

Chemical Property:

• PSA: 76.07000
• LogP: 1.20530
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

(2S)-1-tert-Butyl 2-ethyl 5-hydroxypyrrolidine-1,2-dicarboxylate 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,2-Pyrrolidinedicarboxylic acid, 5-hydroxy-, 1-(1,1-diMethylethyl) 2-ethyl ester, (2S)-

There total 4 articles about 1,2-Pyrrolidinedicarboxylic acid, 5-hydroxy-, 1-(1,1-diMethylethyl) 2-ethyl ester, (2S)- 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: 99.0%

(S)-ethyl N-tert-butoxycarbonylpyroglutamate (144978-35-8,144978-12-1,251924-83-1) → 5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (194594-23-5)

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/0040-4039(94)80043-X

Reference yield:

ethyl (S)-pyroglutamate (7149-65-7) → 5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (194594-23-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 3.35 g / DMAP / acetonitrile / 18 h / 20 °C

2: LiEt₃BH / tetrahydrofuran / 1 h / -78 °C

With dmap; lithium triethylborohydride; In tetrahydrofuran; acetonitrile;

DOI:10.1039/b605293b

Reference yield:

L-Pyroglutamic acid (98-79-3) → 5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (194594-23-5)

Guidance literature:

Multi-step reaction with 3 steps

1: SOCl₂ / 0 - 20 °C

2: 3.35 g / DMAP / acetonitrile / 18 h / 20 °C

3: LiEt₃BH / tetrahydrofuran / 1 h / -78 °C

With dmap; thionyl chloride; lithium triethylborohydride; In tetrahydrofuran; acetonitrile;

DOI:10.1039/b605293b

upstream raw materials:

(S)-ethyl N-tert-butoxycarbonylpyroglutamate

L-Pyroglutamic acid

ethyl (S)-pyroglutamate

di-tert-butyl dicarbonate

Downstream raw materials:

(2S)-1-t-butyl 2-ethyl 5-methoxypyrrolidine-1,2-dicarboxylate

3-(6-chloropyridin-3-yloxymethyl)-2-aza-bicyclo[3.1.0]-hexane hydrochloride

2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester 3-ethyl ester

(1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-formic acid ethyl ester

Refernces

• 1、 Collado, Ivan,Ezquerra, Jesus,Vaquero, Juan Jose,Pedregal, Concepcion. "Diastereoselective functionalization of 5-hydroxy prolinates by tandem Horner-Emmons-Michael reaction". . p. 8037 - 8040. Retrieved 1994.
• 2、 Nirogi, Ramakrishna,Mohammed, Abdul Rasheed,Shinde, Anil K.,Ravella, Srinivasa Rao,Bogaraju, Narsimha,Subramanian, Ramkumar,Mekala, Venkat Reddy,Palacharla, Raghava Choudary,Muddana, Nageswararao,Thentu, Jagadeesh Babu,Bhyrapuneni, Gopinadh,Abraham, Renny,Jasti, Venkat. "Discovery and Development of 3-(6-Chloropyridine-3-yloxymethyl)-2-azabicyclo[3.1.0]hexane Hydrochloride (SUVN-911): A Novel, Potent, Selective, and Orally Active Neuronal Nicotinic Acetylcholine α4β2 Receptor Antagonist for the Treatment of Depression". . p. 2833 - 2853. Retrieved 2020/03/05.
• 3、 Feng, Minghao,Jiang, Xuefeng. "Stereoselective construction of a key hydroindole precursor of epidithiodiketopiperazine (ETP) natural products". supporting information. p. 9690 - 9692. Retrieved 2014/08/18.