(S)-2-Formyl-pyrrolidine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (S)-2-Formyl-pyrrolidine-1-carboxylic acid benzyl ester
• CAS No.: 71461-30-8
• Molecular Formula: C13H15NO3
• Molecular Weight: 233.267
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID90471765
• Nikkaji Number: J246.220F
• Wikidata: Q72442121
• Mol file: 71461-30-8.mol

Synonyms:71461-30-8;(S)-2-Formyl-pyrrolidine-1-carboxylic acid benzyl ester;N-Cbz-L-prolinal;benzyl (2s)-2-formylpyrrolidine-1-carboxylate;(2S)-1-Cbz-2-formylpyrrolidine;Benzyl (S)-2-formylpyrrolidine-1-carboxylate;MFCD17214732;CBZ-L-prolinal;N-benzyloxycarbonyl prolinal;SCHEMBL2198909;DTXSID90471765;ASNHSGGMNWXBEI-LBPRGKRZSA-N;AKOS017344706;AM101184;CS-0319523;I11669;A1-35797;(S)-2-Formyl-pyrrolidine-1-carboxylicacidbenzylester

Chemical Property of (S)-2-Formyl-pyrrolidine-1-carboxylic acid benzyl ester

Chemical Property:

• PSA: 46.61000
• Density: 1.263
• 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

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
• Isomeric SMILES: C1C[C@H](N(C1)C(=O)OCC2=CC=CC=C2)C=O

Technology Process of (S)-2-Formyl-pyrrolidine-1-carboxylic acid benzyl ester

There total 37 articles about (S)-2-Formyl-pyrrolidine-1-carboxylic acid benzyl 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: 99.0%

N-Cbz-Prolinol (6216-63-3) → (S)-2-formylpyrrolidine-1-carboxylic acid benzyl ester (71461-30-8)

Guidance literature:

N-Cbz-Prolinol; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 1h; Schlenk technique; Inert atmosphere;

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 1h; Schlenk technique; Inert atmosphere;

DOI:10.3987/COM-18-S(F)4

Reference yield: 95.0%

N-carbobenzyloxy-L-proline methyl ester (5211-23-4) → (S)-2-formylpyrrolidine-1-carboxylic acid benzyl ester (71461-30-8)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at -78 ℃; for 3h;

DOI:10.1016/S0968-0896(03)00396-1

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;

upstream raw materials:

N-Cbz-Prolinol

N-carbobenzyloxy-L-proline methyl ester

N-Benzyloxycarbonyl-L-proline

1,2-pyrrolidinedicarboxylic acid 2-ethyl 1-(phenylmethyl) ester

Downstream raw materials:

(2S,1'S,2'S)-N-(Benzyloxycarbonyl)-2-<1'-hydroxy-2'-(phenylthio)-3'-butenyl>pyrrolidine

(2S,1'R,2'R)-N-(Benzyloxycarbonyl)-2-<1'-hydroxy-2'-(phenylthio)-3'-butenyl>pyrrolidine

Z-D-prolinal semicarbazone

benzyl (2S)-2-[di(ethylsulfanyl)methyl]tetrahydro-1H-1-pyrrolecarboxylate

Refernces

• 1、 Garbacz, Mateusz,Stecko, Sebastian. "Synthesis of chiral branched allylamines through dual photoredox/nickel catalysis". . p. 8578 - 8585. Retrieved 2021/10/20.
• 2、 Shibuya, Masatoshi,Furukawa, Keisuke,Yamamoto, Yoshihiko. "Selective Aerobic Oxidation of Primary Alcohols to Aldehydes". . p. 1554 - 1557. Retrieved 2017/08/11.