(2R,4S)-1-tert-Butyl 2-methyl 4-aminopyrrolidine-1,2-dicarboxylate

Base Information

• Chemical Name: (2R,4S)-1-tert-Butyl 2-methyl 4-aminopyrrolidine-1,2-dicarboxylate
• CAS No.: 254881-77-1
• Molecular Formula: C11H20N2O4
• Molecular Weight: 244.291
• Hs Code.: 2922498590
• European Community (EC) Number: 815-201-6
• Wikidata: Q76139759
• Mol file: 254881-77-1.mol

Synonyms:254881-77-1;(2R,4S)-1-tert-Butyl 2-methyl 4-aminopyrrolidine-1,2-dicarboxylate;Methyl (2R,4S)-4-Amino-1-Boc-2-pyrrolidinecarboxylate;Methyl (2R,4S)-4-aminopyrrolidine-2-carboxylate, N1-BOC protected;1-O-tert-butyl 2-O-methyl (2R,4S)-4-aminopyrrolidine-1,2-dicarboxylate;MFCD08704545;1-tert-Butyl 2-methyl (2R,4S)-4-aminopyrrolidine-1,2-dicarboxylate;1,2-Pyrrolidinedicarboxylic acid, 4-amino-, 1-(1,1-dimethylethyl) 2-methyl ester, (2R,4S)-;N-Boc-(2R,4S)-4-Amino-D-proline methyl ester;SCHEMBL1267008;AMY18856;AKOS005258639;AKOS015912027;CS-W023214;DS-13099;A5137;EN300-189908;W-206956;trans-4-amino-n-tert-butoxycarbonyl-d-proline methyl ester;(2R,4S)-1-tert-Butyl2-methyl4-aminopyrrolidine-1,2-dicarboxylate;(2R,4S)-4-AMINO-1-BOC-PYRROLIDINE-2-CARBOXYLIC ACID METHYL ESTER;1-tert-Butyl 2-methyl (2R,4S)-4-amino-1,2-pyrrolidinedicarboxylate;Methyl (2R,4S)-1-(tert-butoxycarbonyl)-4-aMinopyrrolidine-2-carboxylate;(2R,4S)-4-aminopyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Chemical Property of (2R,4S)-1-tert-Butyl 2-methyl 4-aminopyrrolidine-1,2-dicarboxylate

Chemical Property:

• Refractive Index: 1.507
• Boiling Point: 320.7 °C at 760 mmHg
• PKA: 9.05±0.40(Predicted)
• Flash Point: 147.7 °C
• PSA: 81.86000
• Density: 1.152 g/cm³
• LogP: 1.13430
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 244.14230712
• Heavy Atom Count: 17
• Complexity: 311

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl (2R,4S)-4-aminopyrrolidine-2-carboxylate, N1-Boc protected ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC(CC1C(=O)OC)N
• Isomeric SMILES: CC(C)(C)OC(=O)N1C[C@H](C[C@@H]1C(=O)OC)N
• Use Description: (2R,4S)-1-tert-Butyl 2-methyl 4-aminopyrrolidine-1,2-dicarboxylate is a chemical compound with diverse applications in various fields. In the pharmaceutical industry, it serves as a critical intermediate in the synthesis of drugs and pharmaceutical compounds, particularly those used in the treatment of neurological and psychiatric disorders. Its unique chemical structure makes it valuable for building complex molecules with potential therapeutic properties. In analytical chemistry, this compound can be used as a reference standard for the identification and quantification of related substances in drug formulations, ensuring quality control and regulatory compliance. Additionally, in academic research, it acts as a versatile building block for the creation of complex organic molecules, facilitating studies in organic chemistry and chemical biology. Its multifaceted utility underscores its importance in advancing drug discovery, analytical techniques, and chemical research across these industries.

Technology Process of (2R,4S)-1-tert-Butyl 2-methyl 4-aminopyrrolidine-1,2-dicarboxylate

There total 8 articles about (2R,4S)-1-tert-Butyl 2-methyl 4-aminopyrrolidine-1,2-dicarboxylate 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: 89.0%

(2R,4S)-1-tert-butyl 2-methyl 4-azidopyrrolidine-1,2-dicarboxylate (185304-04-5) → 1-tert-butyl 2-methyl (2R,4S)-4-aminopyrrolidine-1,2-dicarboxylate (254881-77-1,1018667-18-9)

Guidance literature:

With palladium on activated charcoal; hydrogen; In methanol; at 20 ℃; for 15h;

Reference yield:

(2R,4R)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate (114676-69-6) → 1-tert-butyl 2-methyl (2R,4S)-4-aminopyrrolidine-1,2-dicarboxylate (254881-77-1,1018667-18-9)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / CH₂Cl₂ / 20 °C

2: 59 percent / NaN₃ / dimethylformamide / 26 h / 55 °C

3: 61 percent / H₂; HCOOH / 10percent Pd/C / ethanol; tetrahydrofuran / 16 h / 2792.67 Torr

With formic acid; sodium azide; hydrogen; triethylamine; 10percent Pd/C; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm000246e

Reference yield:

1N-tert-butoxycarbonyl-2(R)-carbomethoxy-4(R)-methanesulfonylpyrrolidine (148017-26-9) → 1-tert-butyl 2-methyl (2R,4S)-4-aminopyrrolidine-1,2-dicarboxylate (254881-77-1,1018667-18-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 59 percent / NaN₃ / dimethylformamide / 26 h / 55 °C

2: 61 percent / H₂; HCOOH / 10percent Pd/C / ethanol; tetrahydrofuran / 16 h / 2792.67 Torr

With formic acid; sodium azide; hydrogen; 10percent Pd/C; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm000246e

upstream raw materials:

(2R,4S)-1-tert-butyl 2-methyl 4-azidopyrrolidine-1,2-dicarboxylate

di-tert-butyl dicarbonate

(2R,4R)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

(2R,4R)-4-hydroxy-2-methoxycarbonylpyrrolidine hydrochloride

Downstream raw materials:

1N-tert-butoxycarbonyl-2(R)-carbomethoxy-4(S)-(pyrrolidin-1N-yl)pyrrolidine

1N-tert-butoxycarbonyl-2(R)-carbomethoxy-4(S)-(γ-chlorosulfonamido)pyrrolidine

1N-tert-butoxycarbonyl-2(R)-carbomethoxy-4(S)-(γ-sultam-1N-yl)pyrrolidine

1N-(4-phenoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-(pyrrolidin-1N-yl)pyrrolidine

Refernces

• 1、 -. "HETEROAROMATIC DERIVATIVES AND PHARMACEUTICAL APPLICATIONS THEREOF". Paragraph 00803. . Retrieved 2016/05/02.
• 2、 -. "MELANOCORTIN RECEPTOR AGONISTS". Page/Page column 22-23. . Retrieved 2010/06/15.