(2S,5S)-1-(Tert-butoxycarbonyl)-5-methylpyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (2S,5S)-1-(Tert-butoxycarbonyl)-5-methylpyrrolidine-2-carboxylic acid
• CAS No.: 334769-80-1
• Molecular Formula: C11H19NO4
• Molecular Weight: 229.276
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID00573547
• Nikkaji Number: J1.400.912D
• Wikidata: Q72450067
• Mol file: 334769-80-1.mol

Synonyms:334769-80-1;(2S,5S)-1-(TERT-BUTOXYCARBONYL)-5-METHYLPYRROLIDINE-2-CARBOXYLIC ACID;(2S,5S)-N-Boc-5-methylpyrrolidine-2-carboxylic acid;(2S,5S)-5-methyl-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid;(2S,5S)-1-BOC-5-methylpyrrolidine-2-carboxylic acid;296775-05-8;MFCD13185989;(5s)-1-(tert-butoxycarbonyl)-5-methyl-l-proline;SCHEMBL192488;AMY4212;DTXSID00573547;BSAYEGDCKUEPNE-YUMQZZPRSA-N;CS-D0422;(2S,5S)-1-(tert-Butoxycarbonyl)-5-methylpyrrolidine-2-carboxylicacid;AKOS016007301;DS-16834;(2S,5S)-Boc-5-methylpyrrolidine-2-carboxylic acid;A1-01614;(2S,55)-1-(tert-butoxycarbonyl)-5-methylpyrrolidine-2-carboxylic acid;(2S,5S)-5-methyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

Chemical Property of (2S,5S)-1-(Tert-butoxycarbonyl)-5-methylpyrrolidine-2-carboxylic acid

Chemical Property:

• Refractive Index: 1.49
• Boiling Point: 343.2 °C at 760 mmHg
• PKA: 4.02±0.40(Predicted)
• Flash Point: 161.4 °C
• PSA: 66.84000
• Density: 1.15 g/cm³
• LogP: 1.79690
• Storage Temp.: 2-8°C
• 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:

97% ^*data from raw suppliers

(2S,5S)-1-(tert-Butoxycarbonyl)-5-methylpyrrolidine-2-carboxylicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(N1C(=O)OC(C)(C)C)C(=O)O
• Isomeric SMILES: C[C@H]1CC[C@H](N1C(=O)OC(C)(C)C)C(=O)O

Technology Process of (2S,5S)-1-(Tert-butoxycarbonyl)-5-methylpyrrolidine-2-carboxylic acid

There total 20 articles about (2S,5S)-1-(Tert-butoxycarbonyl)-5-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%

(2S,5S)-5-methyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (676560-83-1) → (2S,5S)-5-methyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (334769-80-1,1657030-28-8)

Guidance literature:

With lithium hydroxide monohydrate; In ethanol; water; for 16h;

Reference yield: 79.0%

(2S,5S)-1-tert-butyl 2-methyl 5-methylpyrrolidine-1,2-dicarboxylate → (2S,5S)-5-methyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (334769-80-1,1657030-28-8)

Guidance literature:

(2S,5S)-1-tert-butyl 2-methyl 5-methylpyrrolidine-1,2-dicarboxylate; With lithium hydroxide; In tetrahydrofuran;

With hydrogenchloride; In tetrahydrofuran; water; pH=4;

Reference yield:

(S)-5-methyl-3,4-dihydro-2H-pyrrole-2-carboxylic acid ethyl ester (896733-29-2) → (2S,5S)-5-methyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (334769-80-1,1657030-28-8)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / Pd/C / ethanol / 20 °C / 3102.89 Torr

2: 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 20 °C

3: aq. LiOH / ethanol / 4 h / 20 °C

With dmap; lithium hydroxide; hydrogen; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane;

DOI:10.1021/jm051283e

upstream raw materials:

(2S,5S)-5-methyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

(S)-5-methyl-3,4-dihydro-2H-pyrrole-2-carboxylic acid ethyl ester

(S)-2-(tert-butoxycarbonylamino)-5-oxohexanoic acid ethyl ester

(S)-ethyl N-tert-butoxycarbonylpyroglutamate

Downstream raw materials:

(2S,5S)-5-methyl-pyrrolidine-1,2-dicarboxylic acid 2-[2-(4-bromo-phenyl)-2-oxo-ethyl]ester 1-tert-butyl ester

C₂₁H₂₇BrN₄O₃

methyl ((S)-3-methyl-1-((2S,5S)-2-methyl-5-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-1-oxobutan-2-yl)carbamate

(5S)-1-{[(5R,6S)-5,6-bis(4-chlorophenyl)-3-isopropyl-6-methyl-5,6-dihydroimidazo[2,1-b][1,3]thiazol-2-yl]carbonyl}-N,N,5-trimethyl-L-prolinamide