(S)-1-Cbz-3-Aminopyrrolidine

Base Information

• Chemical Name: (S)-1-Cbz-3-Aminopyrrolidine
• CAS No.: 122536-72-5
• Molecular Formula: C12H16N2O2
• Molecular Weight: 220.271
• Hs Code.: 29339900
• European Community (EC) Number: 693-371-9
• DSSTox Substance ID: DTXSID40364012
• Wikidata: Q72516002
• Mol file: 122536-72-5.mol

Synonyms:122536-72-5;(S)-1-Cbz-3-Aminopyrrolidine;(S)-(+)-1-Cbz-3-aminopyrrolidine;(S)-3-AMINO-1-CBZ-PYRROLIDINE;benzyl (3S)-3-aminopyrrolidine-1-carboxylate;(S)-3-Amino-pyrrolidine-1-carboxylic acid benzyl ester;MFCD06858462;1-Pyrrolidinecarboxylic acid, 3-amino-, phenylmethyl ester, (S)-;1-Pyrrolidinecarboxylic acid, 3-amino-, phenylmethyl ester, (3S)-;SCHEMBL1189968;(3S)-1-Cbz-3-aminopyrrolidine;DTXSID40364012;(3S)-1-Cbz-3-amino-pyrrolidine;AKOS005258644;AKOS015889707;AC-7176;AM91185;CS-W013140;AS-80278;TS-03148;(S)-(+)-1-Cbz-3-aminopyrrolidine, 97%;(S)-benzyl 3-aminopyrrolidine-1-carboxylate;A2580;P10427;J-004818;phenylmethyl (3S)-3-amino-1-pyrrolidinecarboxylate;(S)-3-AMINO-1-(BENZYLOXYCARBONYL)PYRROLIDINE;(S)-3-aminopyrrolidine-1-carboxylic acid benzyl ester;(3S)-3-amino-pyrrolidine-1-carboxylic acid, benzyl ester;(S)-(+)-3-AMINO-1-(BENZYLOXYCARBONYL)PYRROLIDINE;(S)-3-Amino-1-pyrrolidinecarboxylic acid, phenylmethyl ester

Chemical Property of (S)-1-Cbz-3-Aminopyrrolidine

Chemical Property:

• Vapor Pressure: 4.04E-05mmHg at 25°C
• Melting Point: 310-316℃
• Refractive Index: n20/D 1.548
• Boiling Point: 351.7 °C at 760 mmHg
• PKA: 9.52±0.20(Predicted)
• Flash Point: 166.5 °C
• PSA: 55.56000
• Density: 1.155 g/cm³
• LogP: 1.99440
• Sensitive.: Air Sensitive
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 220.121177757
• Heavy Atom Count: 16
• Complexity: 239

Purity/Quality:

99% ^*data from raw suppliers

(S)-3-Amino-1-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(CC1N)C(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C1CN(C[C@H]1N)C(=O)OCC2=CC=CC=C2

Technology Process of (S)-1-Cbz-3-Aminopyrrolidine

There total 5 articles about (S)-1-Cbz-3-Aminopyrrolidine 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: 100.0%

(S)-3-<<(1,1-dimethylethoxy)carbonyl>amino>-1-pyrrolidinecarboxylic acid phenylmethyl ester (122536-74-7) → (S)-3-amino-1-pyrrolidinecarboxylic acid phenylmethyl ester (122536-72-5)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; dichloromethane; at 20 ℃; for 2h;

Reference yield: 95.0%

(S)-3-azido-1-pyrrolidinecarboxylic acid phenylmethyl ester (122536-70-3) → (S)-3-amino-1-pyrrolidinecarboxylic acid phenylmethyl ester (122536-72-5)

Guidance literature:

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

DOI:10.1021/jm00088a011

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (S)-3-amino-1-pyrrolidinecarboxylic acid phenylmethyl ester (122536-72-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / 10percent aq. NaOH / 2 h / 5 °C

2: 91 percent / pyridine / 2 h / 5 °C

3: 98 percent / sodium azide / dimethylformamide / 2 h / 100 °C

4: 95 percent / H₂ / Raney nickel / methanol / 21.5 h / 21.5 - 25 °C / 2585.7 Torr

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

DOI:10.1021/jm00088a011

upstream raw materials:

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

benzyl chloroformate

(3R)-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

(R)-3-<(methylsulfonyl)oxy>-1-pyrrolidinecarboxylic acid phenylmethyl ester

Downstream raw materials:

(S)-3-<<(1,1-dimethylethoxy)carbonyl>amino>-1-pyrrolidinecarboxylic acid phenylmethyl ester

*,R^*)>-3-<<2-<<(1,1-dimethylethoxy)carbonyl>amino>-1-oxopropyl>amino>-1-pyrrolidinecarboxylic acid phenylmethyl ester

(3S)-3-cyclohexylamino-pyrrolidine-1-carboxylic acid benzyl ester

(S)-1-(benzyloxycarbonyl)-3-(N,N-diethylamino)pyrrolidine