(R)-Tert-butyl 3-phenylpiperazine-1-carboxylate

Base Information

• Chemical Name: (R)-Tert-butyl 3-phenylpiperazine-1-carboxylate
• CAS No.: 1240584-34-2
• Molecular Formula: C15H22N2O2
• Molecular Weight: 262.352
• Hs Code.: 2933599590
• European Community (EC) Number: 835-718-0,949-005-8
• DSSTox Substance ID: DTXSID80426749
• Nikkaji Number: J3.107.024D
• Wikidata: Q72498209
• ChEMBL ID: CHEMBL5008993
• Mol file: 1240584-34-2.mol

Synonyms:1240584-34-2;(R)-TERT-BUTYL 3-PHENYLPIPERAZINE-1-CARBOXYLATE;tert-butyl (3R)-3-phenylpiperazine-1-carboxylate;tert-Butyl (R)-3-phenylpiperazine-1-carboxylate;R-4-Boc-2-phenylpiperazine;(R)-3-PHENYL-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;(R)-4-Boc-2-phenylpiperazine;rel-tert-butyl (3R)-3-phenylpiperazine-1-carboxylate;(R)-1-Boc-3-Phenylpiperazine;CHEMBL5008993;DTXSID80426749;MFCD08685942;1-Piperazinecarboxylic acid, 3-phenyl-, 1,1-dimethylethyl ester, (3R)-;AKOS022186376;TS-03580;CS-0091687;t-Butyl (R)-3-phenylpiperazine-1-carboxylate;EN300-6501354;EN300-6746236;(R)-TERT-BUTYL3-PHENYLPIPERAZINE-1-CARBOXYLATE;(3R)-3beta-Phenylpiperazine-1-carboxylic acid tert-butyl ester

Chemical Property of (R)-Tert-butyl 3-phenylpiperazine-1-carboxylate

Chemical Property:

• PSA: 41.57000
• Density: 1.071
• LogP: 2.83470
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 262.168127949
• Heavy Atom Count: 19
• Complexity: 306

Purity/Quality:

98% ^*data from raw suppliers

(R)-tert-Butyl3-phenylpiperazine-1-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCNC(C1)C2=CC=CC=C2
• Isomeric SMILES: CC(C)(C)OC(=O)N1CCN[C@@H](C1)C2=CC=CC=C2

Technology Process of (R)-Tert-butyl 3-phenylpiperazine-1-carboxylate

There total 6 articles about (R)-Tert-butyl 3-phenylpiperazine-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: 98.0%

(R)-tert-butyl 4-((R)-2-hydroxy-1-phenylethyl)-3-phenylpiperazine-1-carboxylate (1399859-44-9) → (R)-tert-butyl 3-phenylpiperazine-1-carboxylate (1240584-34-2)

Guidance literature:

With 20% Pd(OH)2/C; hydrogen; In ethanol; at 20 ℃; for 18h; stereoselective reaction;

DOI:10.1016/j.tetlet.2012.07.031

Reference yield:

α-bromoacetophenone (70-11-1) → (R)-tert-butyl 3-phenylpiperazine-1-carboxylate (1240584-34-2)

Guidance literature:

Multi-step reaction with 8 steps

1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 h / 20 °C

2: potassium carbonate / acetonitrile / 20 h / 20 °C

3: (1S)-10-camphorsulfonic acid; (2S)-2-phenylglycinol / toluene / 20 h / Reflux; Dean-Stark

4: titanium tetrachloride; triethylsilane / dichloromethane; tetrahydrofuran / 168 h / -78 - 20 °C

5: lithium aluminium tetrahydride / tetrahydrofuran / 18 h / 0 - 20 °C

6: 10% Pd/C; ammonium formate / ethanol / 4 h / Reflux

7: triethylamine / dichloromethane / 18 h / 20 °C

8: hydrogen; 20% Pd(OH)2/C / ethanol / 18 h / 20 °C

With triethylsilane; lithium aluminium tetrahydride; 10% Pd/C; 20% Pd(OH)2/C; (1S)-10-camphorsulfonic acid; (2S)-2-phenylglycinol; hydrogen; ammonium formate; titanium tetrachloride; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/j.tetlet.2012.07.031

Reference yield:

N-(2-oxo-2-phenylethyl)glycine methyl ester (158457-27-3) → (R)-tert-butyl 3-phenylpiperazine-1-carboxylate (1240584-34-2)

Guidance literature:

Multi-step reaction with 7 steps

1: potassium carbonate / acetonitrile / 20 h / 20 °C

2: (1S)-10-camphorsulfonic acid; (2S)-2-phenylglycinol / toluene / 20 h / Reflux; Dean-Stark

3: titanium tetrachloride; triethylsilane / dichloromethane; tetrahydrofuran / 168 h / -78 - 20 °C

4: lithium aluminium tetrahydride / tetrahydrofuran / 18 h / 0 - 20 °C

5: 10% Pd/C; ammonium formate / ethanol / 4 h / Reflux

6: triethylamine / dichloromethane / 18 h / 20 °C

7: hydrogen; 20% Pd(OH)2/C / ethanol / 18 h / 20 °C

With triethylsilane; lithium aluminium tetrahydride; 10% Pd/C; 20% Pd(OH)2/C; (1S)-10-camphorsulfonic acid; (2S)-2-phenylglycinol; hydrogen; ammonium formate; titanium tetrachloride; potassium carbonate; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; toluene; acetonitrile;

DOI:10.1016/j.tetlet.2012.07.031

upstream raw materials:

(R)-tert-butyl 4-((R)-2-hydroxy-1-phenylethyl)-3-phenylpiperazine-1-carboxylate

α-bromoacetophenone

N-(2-oxo-2-phenylethyl)glycine methyl ester

di-tert-butyl dicarbonate

Refernces