1-O-tert-butyl 2-O,4-O-dimethyl (2S,4R)-pyrrolidine-1,2,4-tricarboxylate

Base Information

• Chemical Name: 1-O-tert-butyl 2-O,4-O-dimethyl (2S,4R)-pyrrolidine-1,2,4-tricarboxylate
• CAS No.: 212266-76-7
• Molecular Formula: C₁₃H₂₁NO₆
• Molecular Weight: 287.313
• DSSTox Substance ID: DTXSID50473846
• Nikkaji Number: J2.751.078G
• Wikidata: Q82303499
• Mol file: 212266-76-7.mol

Synonyms:1-O-tert-butyl 2-O,4-O-dimethyl (2S,4R)-pyrrolidine-1,2,4-tricarboxylate;B-1610;SCHEMBL19853313;DTXSID50473846;F70173

Chemical Property of 1-O-tert-butyl 2-O,4-O-dimethyl (2S,4R)-pyrrolidine-1,2,4-tricarboxylate

Chemical Property:

• Boiling Point: 358.3±42.0 °C(Predicted)
• PKA: -4.73±0.60(Predicted)
• Density: 1.186±0.06 g/cm3(Predicted)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 287.13688739
• Heavy Atom Count: 20
• Complexity: 400

Purity/Quality:

97% ^*data from raw suppliers

(2S,4R)-1-TERT-BUTYL 2,4-DIMETHYLPYRROLIDINE-1,2,4-TRICARBOXYLATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC(CC1C(=O)OC)C(=O)OC
• Isomeric SMILES: CC(C)(C)OC(=O)N1C[C@@H](C[C@H]1C(=O)OC)C(=O)OC

Technology Process of 1-O-tert-butyl 2-O,4-O-dimethyl (2S,4R)-pyrrolidine-1,2,4-tricarboxylate

There total 20 articles about 1-O-tert-butyl 2-O,4-O-dimethyl (2S,4R)-pyrrolidine-1,2,4-tricarboxylate 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:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → 1-(tert-butyl) 2,4-dimethyl (2S,4R)-pyrrolidine-1,2,4-tricarboxylate (212266-76-7)

Guidance literature:

Multi-step reaction with 5 steps

1: triethylamine / dichloromethane / 16.5 h / 0 - 25 °C

2: triethylamine / dichloromethane / 16 h / 0 - 25 °C

3: dimethyl sulfoxide / 16 h / 80 °C

4: water; sodium hydroxide / tetrahydrofuran / 16 h

5: potassium carbonate / N,N-dimethyl-formamide / 16 h / 0 - 25 °C

With water; potassium carbonate; triethylamine; sodium hydroxide; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

Reference yield:

(2S,4R)-1-(tert-butoxycarbonyl)pyrrolidine-2,4-dicarboxylic acid + methyl iodide (74-88-4) → 1-(tert-butyl) 2,4-dimethyl (2S,4R)-pyrrolidine-1,2,4-tricarboxylate (212266-76-7)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 25 ℃; for 16h;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 1-(tert-butyl) 2,4-dimethyl (2S,4R)-pyrrolidine-1,2,4-tricarboxylate (212266-76-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / H₂ / 10percent Pd/C / methanol / 3102.9 Torr / Ambient temperature

2: 96 percent / 6percent Na-Hg, Na₂HPO₄ / methanol / 2 h / 0 °C

3: TEMPO, NaOCl, KBr, 5percent NaHCO₃ / acetone / 2 h / 0 °C

4: acetone

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; disodium hydrogenphosphate; sodium amalgam; hydrogen; sodium hydrogencarbonate; potassium bromide; palladium on activated charcoal; In methanol; acetone;

DOI:10.1016/S0040-4039(98)01171-X

upstream raw materials:

diazomethane

di-tert-butyl dicarbonate

((R)-2-Benzenesulfonyl-1-benzyloxymethyl-ethyl)-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-amine

(2S,4R)-1-tert-butoxycarbonyl-2-hydroxymethyl-4-hydroxymethylpyrrolidine

Downstream raw materials:

(2S,4R)-L-proline-4-carboxylic acid