L-erythro-Ritalinic Acid

Base Information

• Chemical Name: L-erythro-Ritalinic Acid
• CAS No.: 1076192-92-1
• Molecular Formula: C₁₃H₁₇NO₂
• Molecular Weight: 219.283
• DSSTox Substance ID: DTXSID00453052
• Mol file: 1076192-92-1.mol

Synonyms:L-erythro-Ritalinic Acid;1076192-92-1;(2R)-2-phenyl-2-[(2S)-piperidin-2-yl]acetic acid;SCHEMBL20850913;DTXSID00453052

Chemical Property of L-erythro-Ritalinic Acid

Chemical Property:

• PSA: 49.33000
• LogP: 2.32570
• XLogP3: -2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 219.125928785
• Heavy Atom Count: 16
• Complexity: 236

Purity/Quality:

97% ^*data from raw suppliers

L-erythro-RitalinicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCNC(C1)C(C2=CC=CC=C2)C(=O)O
• Isomeric SMILES: C1CCN[C@@H](C1)[C@@H](C2=CC=CC=C2)C(=O)O
• Uses: L-erythro-Ritalinic Acid is used to create enantioselective stationary phases. L-erythro-Ritalinic Acid is a single enantiomer of erythro Ritalinic acid (R533100). A single enantiomer of erythro Ritalinic acid (R533100).

Technology Process of L-erythro-Ritalinic Acid

There total 17 articles about L-erythro-Ritalinic Acid 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: 88.6%

threo-α-phenyl-α-(2-piperidyl)acetamide → Ritalinic acid (19395-41-6,1076192-92-1,54631-24-2,744954-37-8)

Guidance literature:

With hydrogenchloride; water; Reflux;

Reference yield: 88.6%

threo-α-phenyl-α-(2-piperidyl)acetamide → threo-ritalinic acid (1076192-92-1,54631-24-2,744954-37-8)

Guidance literature:

threo-α-phenyl-α-(2-piperidyl)acetamide; With hydrogenchloride; water; for 2 - 6h; Reflux;

With sodium hydroxide; In water; pH=6 - 7;

Reference yield: 40.0%

methylphenidate hydrochloride (298-59-9,19262-68-1,23644-60-2,23655-65-4,29419-95-2,29419-96-3,29419-97-4,56502-30-8) → 2-phenyl-2-(piperidin-2-yl)acetic acid (1076192-92-1,54631-24-2,744954-37-8)

Guidance literature:

With water; potassium hydroxide; In ethanol; at 20 ℃; for 19.3h; pH=5; Reagent/catalyst; Temperature;

DOI:10.1107/S010827011302595X

upstream raw materials:

(±)-erythro/threo-2-phenyl-2-(piperidin-2-yl)acetamide

2-phenyl-2-(pyridin-2-yl)acetamide

phenyl-pyridin-2-yl-acetonitrile

1-piperidin-1-yl-ethanone

Downstream raw materials:

d-threo-ritalinic acid hydrochloride

N,N-dicyclohexylurea

d-threo-ritalinic acid hydrochloride

dexmethylphenidate hydrochloride

Refernces

• 1、 Prashad, Mahavir,Har, Denis,Repic, Oljan,Blacklock, Thomas J.,Giannousis, Peter. "Enzymatic resolution of (±)-threo-methylphenidate". . p. 2133 - 2136. Retrieved 1998.
• 2、 Deng, Hong-Ping,Zhou, Quan,Wu, Jie. "Microtubing-Reactor-Assisted Aliphatic C?H Functionalization with HCl as a Hydrogen-Atom-Transfer Catalyst Precursor in Conjunction with an Organic Photoredox Catalyst". supporting information. p. 12661 - 12665. Retrieved 2018/09/20.