(S)-tert-butyl 1-benzyl-5-oxopyrrolidine-2-carboxylate

Base Information

• Chemical Name: (S)-tert-butyl 1-benzyl-5-oxopyrrolidine-2-carboxylate
• CAS No.: 90741-27-8
• Molecular Formula: C16H21NO3
• Molecular Weight: 275.348
• Hs Code.: 2933790090
• DSSTox Substance ID: DTXSID10441849
• Wikidata: Q82258825
• ChEMBL ID: CHEMBL242220
• Mol file: 90741-27-8.mol

Synonyms:(S)-tert-butyl 1-benzyl-5-oxopyrrolidine-2-carboxylate;90741-27-8;TERT-BUTYL (2S)-1-BENZYL-5-OXOPYRROLIDINE-2-CARBOXYLATE;tert-butyl 1-benzyl-5-oxo-2-pyrrolidinecarboxylate;tert-Butyl (S)-1-benzyl-5-oxopyrrolidine-2-carboxylate;(S)-tert-Butyl1-benzyl-5-oxopyrrolidine-2-carboxylate;CHEMBL242220;SCHEMBL7020132;DTXSID10441849;MFCD11975828;AKOS016013253;CS-0171699;AN-584/43492729

Chemical Property of (S)-tert-butyl 1-benzyl-5-oxopyrrolidine-2-carboxylate

Chemical Property:

• Melting Point: 73-74℃
• PSA: 46.61000
• LogP: 2.45720
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 275.15214353
• Heavy Atom Count: 20
• Complexity: 366

Purity/Quality:

97% ^*data from raw suppliers

(S)-tert-butyl1-benzyl-5-oxopyrrolidine-2-carboxylate 98 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C1CCC(=O)N1CC2=CC=CC=C2
• Isomeric SMILES: CC(C)(C)OC(=O)[C@@H]1CCC(=O)N1CC2=CC=CC=C2

Technology Process of (S)-tert-butyl 1-benzyl-5-oxopyrrolidine-2-carboxylate

There total 13 articles about (S)-tert-butyl 1-benzyl-5-oxopyrrolidine-2-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: 81.0%

L-t-butyl pyroglutamate (35418-16-7,85136-12-5) + benzyl bromide (100-39-0) → (S)-tert-butyl 1-benzyl-5-oxopyrrolidine-2-carboxylate (90741-27-8)

Guidance literature:

L-t-butyl pyroglutamate; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 0.0833333h;

benzyl bromide; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1016/S0040-4020(01)00684-6

Reference yield: 81.0%

L-t-butyl pyroglutamate (35418-16-7,85136-12-5) → (S)-tert-butyl 1-benzyl-5-oxopyrrolidine-2-carboxylate (90741-27-8)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 1h; Heating;

DOI:10.1016/S0040-4020(03)00420-4

Reference yield: 60.0%

N-benzyl-L-pyroglutamic acid (38854-94-3,78964-11-1,7535-59-3) + tert-butyl alcohol (75-65-0) → (S)-tert-butyl 1-benzyl-5-oxopyrrolidine-2-carboxylate (90741-27-8)

Guidance literature:

N-benzyl-L-pyroglutamic acid; With oxalyl dichloride; In N,N-dimethyl-formamide; acetonitrile; at 0 ℃; for 0.25h; Inert atmosphere;

tert-butyl alcohol; With pyridine; In N,N-dimethyl-formamide; acetonitrile; at 20 ℃; for 15h;

upstream raw materials:

tert-butyl alcohol

(S)-N-benzyl-5-thioxoproline tert-butyl ester

Trifluoro-methanesulfonic acid 6-methyl-2-oxo-tetrahydro-pyran-3-yl ester

L-t-butyl pyroglutamate

Downstream raw materials:

N-benzyl-L-pyroglutamic acid

(2S)-1-benzyl-(E)-5-<(methoxycarbonyl)methylidene>proline tert-butyl ester

(S)-N-benzyl-5-thioxoproline tert-butyl ester