1-[(Benzyloxy)carbonyl]pyrrolidin-3-aminium

Base Information

• Chemical Name: 1-[(Benzyloxy)carbonyl]pyrrolidin-3-aminium
• CAS No.: 122536-73-6
• Molecular Formula: C12H16N2O2
• Molecular Weight: 220.271
• Hs Code.: 29339900
• DSSTox Substance ID: DTXSID00924196
• Wikidata: Q72516005
• Mol file: 122536-73-6.mol

Synonyms:DTXSID00924196;1-[(Benzyloxy)carbonyl]pyrrolidin-3-aminium

Chemical Property of 1-[(Benzyloxy)carbonyl]pyrrolidin-3-aminium

Chemical Property:

• Vapor Pressure: 3.37E-06mmHg at 25°C
• Melting Point: 310-316℃
• Refractive Index: n20/D 1.548
• Boiling Point: 351.7 °C at 760 mmHg
• Flash Point: 166.5 °C
• PSA: 55.56000
• Density: 1.186 g/cm³
• LogP: 1.99440
• Sensitive.: Air Sensitive
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 221.129002789
• Heavy Atom Count: 16
• Complexity: 239

Purity/Quality:

99% ^*data from raw suppliers

(R)-3-Amino-1-N-CBZ-Pyrrolidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CC1[NH3+])C(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C1CN(C[C@@H]1[NH3+])C(=O)OCC2=CC=CC=C2
• Uses: (R)-(?)-1-Cbz-3-aminopyrrolidine can be used:In one of the key synthetic steps for the preparations of AZ82, a KIFC1-specific inhibitor for cancer therapy.As a key intermediate in the synthesis of N6-substituted adenosine analogs as potent A1AR agonists.

Technology Process of 1-[(Benzyloxy)carbonyl]pyrrolidin-3-aminium

There total 7 articles about 1-[(Benzyloxy)carbonyl]pyrrolidin-3-aminium 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%

dibenzyl dicarbonate (31139-36-3) + (R)-pyrrolidin-3-amine (116183-82-5) → benzyl (R)-3-amino-pyrrolidine-1-carboxylate (122536-73-6)

Guidance literature:

With hydrogenchloride; In methanol; at 0 ℃; for 2.5h;

DOI:10.1016/j.bmcl.2007.10.028

Reference yield:

(R)-3-azido-1-pyrrolidinecarboxylic acid phenylmethyl ester (122536-71-4) → benzyl (R)-3-amino-pyrrolidine-1-carboxylate (122536-73-6)

Guidance literature:

With hydrogen; nickel; In methanol; at 21.5 - 25 ℃; for 21.5h; under 2585.7 Torr;

DOI:10.1021/jm00088a011

Reference yield:

(S)-3-<(methylsulfonyl)oxy>-1-pyrrolidinecarboxylic acid phenylmethyl ester (122536-69-0) → benzyl (R)-3-amino-pyrrolidine-1-carboxylate (122536-73-6)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium azide / dimethylformamide / 2 h / 100 °C

2: H₂ / Raney nickel / methanol / 21.5 h / 21.5 - 25 °C / 2585.7 Torr

With sodium azide; hydrogen; nickel; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00088a011

upstream raw materials:

(R)-3-azido-1-pyrrolidinecarboxylic acid phenylmethyl ester

dibenzyl dicarbonate

(R)-pyrrolidin-3-amine

(S)-3-hydroxy-1-pyrrolidinecarboxylic acid phenylmethyl ester

Downstream raw materials:

Benzyl (3R)-3-[(tert-butoxycarbonyl)amino]pyrrolidine-1-carboxylate

(R)-3-((S)-2-tert-Butoxycarbonylamino-propionylamino)-pyrrolidine-1-carboxylic acid benzyl ester