Benzyl 2-formylpyrrolidine-1-carboxylate

Base Information

• Chemical Name: Benzyl 2-formylpyrrolidine-1-carboxylate
• CAS No.: 105706-84-1
• Molecular Formula: C13H15NO3
• Molecular Weight: 233.267
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID20453918
• Nikkaji Number: J1.506.863I
• Mol file: 105706-84-1.mol

Synonyms:105706-84-1;Benzyl 2-formylpyrrolidine-1-carboxylate;1-Cbz-2-formylpyrrolidine;2-Formyl-pyrrolidine-1-carboxylic acid benzyl ester;Pyrrolidine-2-carboxaldehyde, N-CBZ protected;SCHEMBL2198876;DTXSID20453918;ASNHSGGMNWXBEI-UHFFFAOYSA-N;MFCD04115610;AKOS015951463;AB91758;AM90545;PS-5692;SB46481;benzyl-2-formylpyrrolidine-1-carboxylate;N-carbobenzyloxypyrrolidine-2-carboxaldehyde;CS-0313319;FT-0761821;FT-0772992;(+/-)-N-benzyloxycarbonyl-2-formylpyrrolidine;1-Benzyloxycarbonylpyrrolidine-2-carboxaldehyde;F79978;2-Formyl-pyrrolidine-1-carboxylicacidbenzylester;2-Formylpyrrolidine-1-carboxylic acid benzyl ester;J-001472

Chemical Property of Benzyl 2-formylpyrrolidine-1-carboxylate

Chemical Property:

• PSA: 46.61000
• LogP: 1.92440
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 233.10519334
• Heavy Atom Count: 17
• Complexity: 274

Purity/Quality:

≥95% ^*data from raw suppliers

Benzyl2-Formylpyrrolidine-1-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(N(C1)C(=O)OCC2=CC=CC=C2)C=O

Technology Process of Benzyl 2-formylpyrrolidine-1-carboxylate

There total 19 articles about Benzyl 2-formylpyrrolidine-1-carboxylate 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: 84.7%

(2R)-(+)-phenylmethyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate (72597-18-3) → (2R)-(+)-phenylmethyl 2-formylpyrrolidine-1-carboxylate (50463-82-6,71461-30-8,105706-84-1,143393-11-7)

Guidance literature:

(2R)-(+)-phenylmethyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate; With phosgene; In dichloromethane; dimethyl sulfoxide; at -78 ℃; for 0.5h;

With triethylamine; In dichloromethane; dimethyl sulfoxide; at 20 ℃; for 1h;

Reference yield: 80.0%

(R)-2-(Bis-ethylsulfanyl-methyl)-pyrrolidine-1-carboxylic acid benzyl ester → (2R)-(+)-phenylmethyl 2-formylpyrrolidine-1-carboxylate (50463-82-6,71461-30-8,105706-84-1,143393-11-7)

Guidance literature:

With iron(III) chloride; In dichloromethane; at 20 ℃; for 0.25h;

Reference yield: 79.0%

(R)-1-benzyloxycarbonyl-2-[(S)-1,2-dihydroxyethyl]pyrrolidine (200499-58-7) → (2R)-(+)-phenylmethyl 2-formylpyrrolidine-1-carboxylate (50463-82-6,71461-30-8,105706-84-1,143393-11-7)

Guidance literature:

With sodium periodate; In methanol; for 2h;

DOI:10.1039/a704915c

upstream raw materials:

(S)-2-(3,5-Dimethyl-pyrazole-1-carbonyl)-pyrrolidine-1-carboxylic acid benzyl ester

N-carbobenzyloxyproline

benzyl chloroformate

rac-Pro-OH

Downstream raw materials:

Z-D-proline

(2R)-(+)-phenylmethyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate

ethyl-3-(N-benzyloxycarbonylpiperid-2-yl)-2-propenoate

ethyl 3-(N-benzyloxycarbonylpyrrolin-2-yl)-2-propenoate

Refernces

• 1、 Tan, Mario A.,Kitajima, Mariko,Kogure, Noriyuki,Nonato, Maribel G.,Takayama, Hiromitsu. "Isolation and total syntheses of two new alkaloids, dubiusamines-A, and -B, from Pandanus dubius". scheme or table. p. 3353 - 3359. Retrieved 2010/06/17.
• 2、 Pallavicini, Marco,Moroni, Barbara,Bolchi, Cristiano,Cilia, Antonio,Clementi, Francesco,Fumagalli, Laura,Gotti, Cecilia,Meneghetti, Fiorella,Riganti, Loredana,Vistoli, Giulio,Valoti, Ermanno. "Synthesis and α4β2 nicotinic affinity of unichiral 5-(2-pyrrolidinyl)oxazolidinones and 2-(2-pyrrolidinyl)benzodioxanes". . p. 5610 - 5615. Retrieved 2007/10/03.