(S)-Tert-butyl 4-benzyl-2-methylpiperazine-1-carboxylate

Base Information

• Chemical Name: (S)-Tert-butyl 4-benzyl-2-methylpiperazine-1-carboxylate
• CAS No.: 169447-69-2
• Molecular Formula: C17H26N2O2
• Molecular Weight: 290.40100
• DSSTox Substance ID: DTXSID80439733
• Nikkaji Number: J2.822.157F
• Wikidata: Q82255780
• Mol file: 169447-69-2.mol

Synonyms:169447-69-2;(S)-TERT-BUTYL 4-BENZYL-2-METHYLPIPERAZINE-1-CARBOXYLATE;TERT-BUTYL (2S)-4-BENZYL-2-METHYLPIPERAZINE-1-CARBOXYLATE;(S)-1-tert-butoxycarbonyl-2-methyl-4-benzylpiperazine;TERT-BUTYL-4-BENZYL-2(R)-METHYL-PIPERAZINECARBOXYLATE;SCHEMBL7968974;DTXSID80439733;AB3319;MFCD09953042;AKOS027252412;4-Benzyl-1-tert-butoxycarbonyl-2(S)-methylpiperazine;(2S)-2beta-Methyl-4-benzylpiperazine-1-carboxylic acid tert-butyl ester

Chemical Property of (S)-Tert-butyl 4-benzyl-2-methylpiperazine-1-carboxylate

Chemical Property:

• PSA: 32.78000
• LogP: 3.00360
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 290.199428076
• Heavy Atom Count: 21
• Complexity: 345

Purity/Quality:

99% ^*data from raw suppliers

(S)-TERT-BUTYL-4-BENZYL-2-METHYLPIPERAZINE-1-CARBOXYLATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CN(CCN1C(=O)OC(C)(C)C)CC2=CC=CC=C2
• Isomeric SMILES: C[C@H]1CN(CCN1C(=O)OC(C)(C)C)CC2=CC=CC=C2

Technology Process of (S)-Tert-butyl 4-benzyl-2-methylpiperazine-1-carboxylate

There total 13 articles about (S)-Tert-butyl 4-benzyl-2-methylpiperazine-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: 99.0%

di-tert-butyl dicarbonate (24424-99-5) + (S)-3-Methyl-1-(phenylmethyl)piperazine (132871-12-6) → tert-Butyl (S)-2-methyl-4-(phenylmethyl)-1-piperazinecarboxylate (169447-69-2)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 20h;

DOI:10.1081/SCC-200036590

Reference yield: 61.0%

tert-butyl (S)-4-benzyl-2-methyl-5-oxopiperazine-1-carboxylate (1004286-93-4) → tert-Butyl (S)-2-methyl-4-(phenylmethyl)-1-piperazinecarboxylate (169447-69-2)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1016/j.tetasy.2009.12.025

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + water (7732-18-5) + (3S)-1-benzyl-3-methylpiperazine-2,5-dione (132871-10-4) → tert-Butyl (S)-2-methyl-4-(phenylmethyl)-1-piperazinecarboxylate (169447-69-2)

Guidance literature:

With sodium hydroxide; sodium hydrogencarbonate; In tetrahydrofuran; hexane; dichloromethane;

upstream raw materials:

di-tert-butyl dicarbonate

(S)-3-Methyl-1-(phenylmethyl)piperazine

methyl (S)-2-(2-chloroacetamido)propanoate

(3S)-1-benzyl-3-methylpiperazine-2,5-dione

Downstream raw materials:

(S)-2-methyl-piperazine-1-carboxylic acid tert-butyl ester

Refernces

• 1、 Firth, James D.,O'Brien, Peter,Ferris, Leigh. "Synthesis of Enantiopure Piperazines via Asymmetric Lithiation-Trapping of N-Boc Piperazines: Unexpected Role of the Electrophile and Distal N-Substituent". . p. 651 - 659. Retrieved 2016/01/29.
• 2、 Liu, Bo,Xu, Guang-Yu,Yang, Chun-Hao,Wu, Xi-Han,Xie, Yu-Yuan. "A novel and facile method to synthesize (R)- and (S)-2-methylpiperazine". . p. 4111 - 4118. Retrieved 2007/10/03.