Methyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylate

Base Information

• Chemical Name: Methyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylate
• CAS No.: 126766-61-8
• Molecular Formula: C₇H₁₄N₂O₃
• Molecular Weight: 174.2
• DSSTox Substance ID: DTXSID90576249
• Wikidata: Q82465828
• Mol file: 126766-61-8.mol

Synonyms:126766-61-8;METHYL (3S)-3-(HYDROXYMETHYL)PIPERAZINE-1-CARBOXYLATE;1-Piperazinecarboxylicacid,3-(hydroxymethyl)-,methylester,(S)-(9CI);URRJXZRIRRSAAC-LURJTMIESA-N;DTXSID90576249;(S)-Methyl 3-(hydroxymethyl)-1-piperazinecarboxylate

Chemical Property of Methyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylate

Chemical Property:

• PSA: 61.80000
• LogP: -0.71440
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 174.10044231
• Heavy Atom Count: 12
• Complexity: 163

Purity/Quality:

(S)-3-(hydroxymethyl)-1-Piperazinecarboxylicacidmethylester 97.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)N1CCNC(C1)CO
• Isomeric SMILES: COC(=O)N1CCN[C@@H](C1)CO

Technology Process of Methyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylate

There total 4 articles about Methyl (3S)-3-(hydroxymethyl)piperazine-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: 83.0%

methyl chloroformate (79-22-1) + (S)-2-piperazinemethanol dihydrochloride (1217482-26-2) → (S)-methyl 3-(hydroxymethyl)-1-piperazinecarboxylate (126766-61-8)

Guidance literature:

In acetonitrile; for 0.5h; Ambient temperature;

DOI:10.1021/jm00067a004

Reference yield:

(S)-4-(phenylmethyl)-2-piperazinemethanol (149715-45-7) → (S)-methyl 3-(hydroxymethyl)-1-piperazinecarboxylate (126766-61-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / H₂, aq. HCl / 10percent Pd/C / tetrahydrofuran / 760 Torr

2: 83 percent / acetonitrile / 0.5 h / Ambient temperature

With hydrogenchloride; hydrogen; palladium on activated charcoal; In tetrahydrofuran; acetonitrile;

DOI:10.1021/jm00067a004

Reference yield:

(R)-3-(hydroxymethyl)-1-(phenylmethyl)-2,5-piperazinedione (149648-95-3) → (S)-methyl 3-(hydroxymethyl)-1-piperazinecarboxylate (126766-61-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / Heating

2: 68 percent / H₂, aq. HCl / 10percent Pd/C / tetrahydrofuran / 760 Torr

3: 83 percent / acetonitrile / 0.5 h / Ambient temperature

With hydrogenchloride; lithium aluminium tetrahydride; hydrogen; palladium on activated charcoal; In tetrahydrofuran; acetonitrile;

DOI:10.1021/jm00067a004

upstream raw materials:

methyl chloroformate

(S)-2-piperazinemethanol dihydrochloride

(S)-4-(phenylmethyl)-2-piperazinemethanol

(R)-3-(hydroxymethyl)-1-(phenylmethyl)-2,5-piperazinedione

Downstream raw materials:

(S)-methyl 4-<(3,4-dichlorophenyl)acetyl>-3-(hydroxymethyl)-1-piperazinecarboxylate

(S)-4-[2-(3,4-Dichloro-phenyl)-acetyl]-3-formyl-piperazine-1-carboxylic acid methyl ester

Refernces