(2S,4R)-1-(Tert-butoxycarbonyl)-4-methylpyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (2S,4R)-1-(Tert-butoxycarbonyl)-4-methylpyrrolidine-2-carboxylic acid
• CAS No.: 364750-80-1
• Molecular Formula: C11H19 N O4
• Molecular Weight: 229.276
• Hs Code.: 2933990090
• European Community (EC) Number: 695-079-7
• DSSTox Substance ID: DTXSID60448106
• Nikkaji Number: J1.912.268I
• Wikidata: Q72450070
• Mol file: 364750-80-1.mol

Synonyms:364750-80-1;(2S,4R)-1-(TERT-BUTOXYCARBONYL)-4-METHYLPYRROLIDINE-2-CARBOXYLIC ACID;(2S,4R)-N-BOC-4-METHYLPYRROLIDINE-2-CARBOXYLIC ACID;(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid;(2S,4R)-4-methyl-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic Acid;(2S,4R)-1-Boc-4-methylpyrrolidine-2-carboxylic acid;(2S,4R)-1-(tert-Butoxycarbonyl)-4-methylpyrrolidine-2-carboxylicacid;SCHEMBL1294186;DTXSID60448106;AMY23734;MFCD13185988;AKOS015991600;SS-4367;A6302;CS-0038277;EN300-7409872;(4R)-1-(tert-Butoxycarbonyl)-4-methyl-L-proline;4beta-Methylpyrrolidine-1,2alpha-dicarboxylic acid 1-tert-butyl ester

Chemical Property of (2S,4R)-1-(Tert-butoxycarbonyl)-4-methylpyrrolidine-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 343 ºC
• PKA: 4.02±0.40(Predicted)
• Flash Point: 161 ºC
• PSA: 66.84000
• Density: 1.150
• LogP: 1.65440
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 229.13140809
• Heavy Atom Count: 16
• Complexity: 295

Purity/Quality:

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

(2S,4R)-N-Boc-4-methylpyrrolidine-2-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC(N(C1)C(=O)OC(C)(C)C)C(=O)O
• Isomeric SMILES: C[C@@H]1C[C@H](N(C1)C(=O)OC(C)(C)C)C(=O)O

Technology Process of (2S,4R)-1-(Tert-butoxycarbonyl)-4-methylpyrrolidine-2-carboxylic acid

There total 40 articles about (2S,4R)-1-(Tert-butoxycarbonyl)-4-methylpyrrolidine-2-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: 100.0%

tert-butyl (2S,4R)-2-(hydroxymethyl)-4-methylpyrrolidine-1-carboxylate (220047-75-6) → (2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid (364750-80-1,871727-77-4)

Guidance literature:

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; In water; acetonitrile; at 20 ℃; for 15h;

DOI:10.3987/COM-18-S(F)8

Reference yield: 44.0%

C11H19NO4 → (2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid (364750-80-1,871727-77-4)

Guidance literature:

C₁₁H₁₉NO₄; With trimethylaluminum; N,O-dimethylhydroxylamine*hydrochloride; In tetrahydrofuran; toluene; at -30 - 23 ℃; for 0.666667h; Inert atmosphere;

With methanesulfonyl chloride; triethylamine; In tetrahydrofuran; at -78 - 23 ℃; for 1h; Further stages; Inert atmosphere;

DOI:10.1021/acs.joc.8b00248

Reference yield:

1-tert-butyl 2-methyl (2S,4R)-4-methylpyrrolidine-1,2-dicarboxylate (138512-74-0) → (2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid (364750-80-1,871727-77-4)

Guidance literature:

With lithium hydroxide monohydrate; In tetrahydrofuran; methanol; water; at 20 ℃; for 14h;

DOI:10.1021/ja210660g

upstream raw materials:

tert-butyl (2S,4R)-2-(hydroxymethyl)-4-methylpyrrolidine-1-carboxylate

L-leucine

di-tert-butyl dicarbonate

tert-butyl (2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylate

Downstream raw materials:

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

(2S,4R)-4-hydroxy-2-pyrrolidinecarboxylic acid hydrochloride

(2S,4R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-methylpyrrolidine-2-carboxylic acid

N-9-fuorenylmethoxycarbonyl-(2S,4R)-4-methylprolyl-(2S,4S)-4-methylprolyl-glycine benzyl ester

Refernces

• 1、 Zwick, Christian R.,Renata, Hans. "Evolution of Biocatalytic and Chemocatalytic C-H Functionalization Strategy in the Synthesis of Manzacidin C". . p. 7407 - 7415. Retrieved 2018/05/29.
• 2、 He, Gang,Zhao, Yingsheng,Zhang, Shuyu,Lu, Chengxi,Chen, Gong. "Highly efficient syntheses of azetidines, pyrrolidines, and indolines via palladium catalyzed intramolecular amination of C(sp3)-H and C(sp2)-H bonds at γ and δ positions". supporting information; experimental part. p. 3 - 6. Retrieved 2012/02/16.