(2S,4R)-1-Boc-4-Benzyloxy-pyrrolidine-2-dicarboxylic acid methyl ester

Base Information

• Chemical Name: (2S,4R)-1-Boc-4-Benzyloxy-pyrrolidine-2-dicarboxylic acid methyl ester
• CAS No.: 136024-60-7
• Molecular Formula: C18H25NO5
• Molecular Weight: 335.4
• DSSTox Substance ID: DTXSID90564803
• Nikkaji Number: J2.237.946A
• Wikidata: Q82449630
• Mol file: 136024-60-7.mol

Synonyms:136024-60-7;(2S,4R)-1-Boc-4-Benzyloxy-pyrrolidine-2-dicarboxylic acid methyl ester;1-O-tert-butyl 2-O-methyl (2S,4R)-4-phenylmethoxypyrrolidine-1,2-dicarboxylate;1-(Tert-butyl) 2-methyl (2S,4R)-4-(benzyloxy)pyrrolidine-1,2-dicarboxylate;AXXKODYHGLJTHX-CABCVRRESA-N;SCHEMBL475487;DTXSID90564803;MFCD11053516;(2S,4R)-4-Benzyloxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester;CS-0445274;(2S,4R)-1-tert-butyl 2-methyl 4-(benzyloxy)pyrrolidine-1,2-dicarboxylate;1-tert-Butyl 2-methyl (2S,4R)-4-(benzyloxy)pyrrolidine-1,2-dicarboxylate

Chemical Property of (2S,4R)-1-Boc-4-Benzyloxy-pyrrolidine-2-dicarboxylic acid methyl ester

Chemical Property:

• PSA: 65.07000
• LogP: 2.69210
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 335.17327290
• Heavy Atom Count: 24
• Complexity: 439

Purity/Quality:

99%min ^*data from raw suppliers

(2S,4R)-4-BENZYLOXY-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 2-METHYL ESTER 95.00% ^*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)OCC2=CC=CC=C2
• Isomeric SMILES: CC(C)(C)OC(=O)N1C[C@@H](C[C@H]1C(=O)OC)OCC2=CC=CC=C2

Technology Process of (2S,4R)-1-Boc-4-Benzyloxy-pyrrolidine-2-dicarboxylic acid methyl ester

There total 5 articles about (2S,4R)-1-Boc-4-Benzyloxy-pyrrolidine-2-dicarboxylic acid methyl ester 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: 97.0%

benzyl bromide (100-39-0) + 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate (74844-91-0) → 1-(tert-butyl) 2-methyl (2S,4R)-4-(benzyloxy)pyrrolidine-1,2-dicarboxylate (136024-60-7)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 16h; Inert atmosphere;

Reference yield:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → 1-(tert-butyl) 2-methyl (2S,4R)-4-(benzyloxy)pyrrolidine-1,2-dicarboxylate (136024-60-7)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine; dmap / dichloromethane / 16 h / 20 °C / Inert atmosphere

2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / Inert atmosphere

With dmap; sodium hydride; triethylamine; In dichloromethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1039/c4cc03660c

Reference yield:

(R)-4-hydroxy-L-proline ethyl ester (1499-56-5,775275-31-5,790644-51-8,754962-86-2) → 1-(tert-butyl) 2-methyl (2S,4R)-4-(benzyloxy)pyrrolidine-1,2-dicarboxylate (136024-60-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / NaH

With sodium hydride;

DOI:10.1016/j.tetlet.2005.09.021

upstream raw materials:

benzyl bromide

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

(R)-4-hydroxy-L-proline ethyl ester

4R-4-hydroxyproline

Downstream raw materials:

(2S,4R)-methyl 4-(benzyloxy)pyrrolidine-2-carboxylate hydrochloride

C₂₂H₃₁N₃O₆

(7R,8aS)-3-allyl-7-(benzyloxy)hexahydropyrrolo[1,2-d][1,2,4]triazine-1,4-dione

(7R)-7-(benzyloxy)-3-(but-3-en-1-yl)hexahydropyrrolo[1,2-d][1,2,4]triazine-1,4-dione

Refernces

• 1、 -. "N-methyl-D-aspartate receptor modulators and methods of making and using same". Page/Page column 51; 53. . Retrieved 2018/06/25.
• 2、 Regenass, Pierre,Margathe, Jean-Fran?ois,Mann, André,Suffert, Jean,Hibert, Marcel,Girard, Nicolas,Bonnet, Dominique. "Diastereoselective synthesis of novel aza-diketopiperazines via a domino cyclohydrocarbonylation/addition process". supporting information. p. 9657 - 9660. Retrieved 2014/08/18.