(3S,6S)-3-(hydroxymethyl)-6-methylpiperazine-2,5-dione

Base Information

• Chemical Name: (3S,6S)-3-(hydroxymethyl)-6-methylpiperazine-2,5-dione
• CAS No.: 155225-26-6
• Molecular Formula: C₆H₁₀N₂O₃
• Molecular Weight: 158.157
• DSSTox Substance ID: DTXSID30428617
• Nikkaji Number: J1.560.246E
• Wikidata: Q82241434
• Mol file: 155225-26-6.mol

Synonyms:Cyclo(-Ala-Ser);155225-26-6;(3S,6S)-3-(hydroxymethyl)-6-methylpiperazine-2,5-dione;Cyclo(L-Ala-L-Ser);Cyclo(Ala-Ser-);SCHEMBL17966419;DTXSID30428617;MFCD00237605;AKOS006274982;AT17303;CS-0181903

Chemical Property of (3S,6S)-3-(hydroxymethyl)-6-methylpiperazine-2,5-dione

Chemical Property:

• Vapor Pressure: 6.68E-15mmHg at 25°C
• Refractive Index: 1.47
• Boiling Point: 560.6°Cat760mmHg
• Flash Point: 292.8°C
• PSA: 78.43000
• Density: 1.215g/cm³
• LogP: -1.36060
• Storage Temp.: -15°C
• XLogP3: -1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 158.06914219
• Heavy Atom Count: 11
• Complexity: 192

Purity/Quality:

99%+, ^*data from raw suppliers

Cyclo(L-Ala-L-Ser) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(=O)NC(C(=O)N1)CO
• Isomeric SMILES: C[C@H]1C(=O)N[C@H](C(=O)N1)CO

Technology Process of (3S,6S)-3-(hydroxymethyl)-6-methylpiperazine-2,5-dione

There total 2 articles about (3S,6S)-3-(hydroxymethyl)-6-methylpiperazine-2,5-dione 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: 85.0%

(S)-N-serine methylester (155225-23-3) → (S)-2-hydroxymethyl-4-methyl-3,6-diketopiperazine (155225-26-6)

Guidance literature:

With cyclohexene; palladium on activated charcoal; In methanol; Heating;

DOI:10.1016/j.tet.2005.06.084

Reference yield:

(S)-3-Hydroxy-2-(2-methylamino-acetylamino)-propionic acid methyl ester → (S)-2-hydroxymethyl-4-methyl-3,6-diketopiperazine (155225-26-6)

Guidance literature:

With methanol; at 62 - 65 ℃; for 110h; Yield given;

DOI:10.1016/S0957-4166(00)80107-X

Reference yield:

(S)-2-hydroxymethyl-4-methyl-3,6-diketopiperazine (155225-26-6) → 3-hydroxymethyl-4-(p-methoxybenzyl)-1-methylpiperazine-2,5-dione (865879-32-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / imidazole / dimethylformamide / 1 h

2: 72 percent / NaH / dimethylformamide / 24 h / 0 °C

3: 83 percent / AcOH / H₂O; tetrahydrofuran / 24 h / Heating

With 1H-imidazole; sodium hydride; acetic acid; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2005.06.084

upstream raw materials:

(S)-N-serine methylester

Downstream raw materials:

3-hydroxymethyl-4-(p-methoxybenzyl)-1-methylpiperazine-2,5-dione

(S)-3-(t-butyldimethylsilanyloxymethyl)-4-(p-methoxybenzyl)-1-methylpiperazine-2,5-dione

Refernces

• 1、 Falorni, Massimo,Satta, Michele,Conti, Sandra,Giacomelli, Giampaolo. "Chiral Ligands Containing Heteroatoms. 11. Optically Active 2-Hydroxymethyl Piperazines as Catalyst in the Enantioselective Addition of Diethylzinc to Benzaldehyde". . p. 2389 - 2398. Retrieved 2007/10/02.