tert-butyl (S)-3-benzyloxycarbonylaminopyrrolidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl (S)-3-benzyloxycarbonylaminopyrrolidine-1-carboxylate
• CAS No.: 247569-07-9
• Molecular Formula: C17H24N2O4
• Molecular Weight: 320.38300
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID30947671
• Wikidata: Q72515947
• Mol file: 247569-07-9.mol

Synonyms:247569-07-9;(S)-3-Cbz-Amino-1-Boc-pyrrolidine;tert-butyl (S)-3-benzyloxycarbonylaminopyrrolidine-1-carboxylate;(S)-tert-Butyl 3-(((benzyloxy)carbonyl)amino)pyrrolidine-1-carboxylate;tert-butyl (3S)-3-(phenylmethoxycarbonylamino)pyrrolidine-1-carboxylate;SCHEMBL6944572;DTXSID30947671;WLSYDQGCKDPQPL-AWEZNQCLSA-N;(S)-3-benzyloxycarbonylamino-1-tert-butoxycarbonylpyrrolidine;(S)-tert-Butyl3-(((benzyloxy)carbonyl)amino)pyrrolidine-1-carboxylate;tert-butyl (3S)-3-{[(benzyloxy)carbonyl]amino}pyrrolidine-1-carboxylate;tert-Butyl 3-{[(benzyloxy)(hydroxy)methylidene]amino}pyrrolidine-1-carboxylate

Chemical Property of tert-butyl (S)-3-benzyloxycarbonylaminopyrrolidine-1-carboxylate

Chemical Property:

• PSA: 67.87000
• Density: 1.17
• LogP: 3.25100
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 320.17360725
• Heavy Atom Count: 23
• Complexity: 413

Purity/Quality:

99% ^*data from raw suppliers

(S)-3-Cbz-amino-1-boc-pyrrolidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCC(C1)NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: CC(C)(C)OC(=O)N1CC[C@@H](C1)NC(=O)OCC2=CC=CC=C2

Technology Process of tert-butyl (S)-3-benzyloxycarbonylaminopyrrolidine-1-carboxylate

There total 18 articles about tert-butyl (S)-3-benzyloxycarbonylaminopyrrolidine-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: 87.2%

benzyl chloroformate (501-53-1,94274-21-2) + 3-amino-1-(t-butoxycarbonyl)pyrrolidine (186550-13-0) → tert-butyl 3-{[(benzyloxy)carbonyl]amino}-1-pyrrolidinecarboxylate (325775-36-8,247569-07-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 3h; Cooling with ice;

DOI:10.1039/c8ob00286j

Reference yield: 80.0%

3-benzyloxycarbonylamino-2-phenylsulfanyl-pyrrolidine-1-carboxylic acid tert-butyl ester (849111-97-3) → tert-butyl (S)-3-(((benzyloxy)carbonyl)amino)pyrrolidine-1-carboxylate (247569-07-9)

Guidance literature:

3-benzyloxycarbonylamino-2-phenylsulfanyl-pyrrolidine-1-carboxylic acid tert-butyl ester; With n-butyllithium; naphthalen-1-yl-lithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

With methanol; In tetrahydrofuran; hexane;

DOI:10.1055/s-2004-837194

Reference yield: 77.0%

benzyl chloroformate (501-53-1,94274-21-2) + (3S)-3-amino-1-(tert-butoxycarbonyl)-pyrrolidine (147081-44-5) → tert-butyl (S)-3-(((benzyloxy)carbonyl)amino)pyrrolidine-1-carboxylate (247569-07-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25 ℃; for 16h; Inert atmosphere;

upstream raw materials:

benzyl alcohol

3-benzyloxycarbonylamino-2-phenylsulfanyl-pyrrolidine-1-carboxylic acid tert-butyl ester

benzyl chloroformate

(3S)-3-amino-1-(tert-butoxycarbonyl)-pyrrolidine

Downstream raw materials:

3-amino-1-(t-butoxycarbonyl)pyrrolidine

1-(cyclopropylmethyl)-N-methylpyrrolidin-3-amine

tert‐butyl 3‐(methylamino)pyrrolidine‐1‐carboxylate