(3R)-3-hydroxy-2-[(1S)-1-phenylethyl]-3H-isoindol-1-one

Base Information

• Chemical Name: (3R)-3-hydroxy-2-[(1S)-1-phenylethyl]-3H-isoindol-1-one
• CAS No.: 503859-63-0
• Molecular Formula: C₁₆H₁₅NO₂
• Molecular Weight: 253.301
• DSSTox Substance ID: DTXSID50476256
• Nikkaji Number: J1.821.994H
• Wikidata: Q82307316
• Mol file: 503859-63-0.mol

Synonyms:CTK1E5752;503859-63-0;DTXSID50476256

Chemical Property of (3R)-3-hydroxy-2-[(1S)-1-phenylethyl]-3H-isoindol-1-one

Chemical Property:

• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 253.110278721
• Heavy Atom Count: 19
• Complexity: 338

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC=CC=C1)N2C(C3=CC=CC=C3C2=O)O
• Isomeric SMILES: C[C@@H](C1=CC=CC=C1)N2[C@@H](C3=CC=CC=C3C2=O)O

Technology Process of (3R)-3-hydroxy-2-[(1S)-1-phenylethyl]-3H-isoindol-1-one

There total 1 articles about (3R)-3-hydroxy-2-[(1S)-1-phenylethyl]-3H-isoindol-1-one 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:

2-((S)-1-phenylethyl)-isoindoline-1,3-dione (3976-26-9) → (1'S,3R)-2,3-dihydro-3-hydroxy-1-(1'-phenylethyl)-1H-isoindol-1-one (503859-63-0) + (1'S,3S)-2,3-dihydro-3-hydroxy-1-(1'-phenylethyl)-1H-isoindol-1-one (503859-65-2)

Guidance literature:

With hydrogenchloride; sodium tetrahydroborate; In methanol; at -5 - 0 ℃; for 0.5h;

DOI:10.3987/com-02-s(m)43

Reference yield:

(1'S,3R)-2,3-dihydro-3-hydroxy-1-(1'-phenylethyl)-1H-isoindol-1-one (503859-63-0) → [(R)-3-Oxo-2-((S)-1-phenyl-ethyl)-2,3-dihydro-1H-isoindol-1-yl]-acetyl chloride

Guidance literature:

Multi-step reaction with 2 steps

1.1: toluene / 12 h / Heating

1.2: aq. potassium carbonate / ethanol / 2 h / Heating

2.1: thionyl chloride / CH₂Cl₂ / 2 h / Heating

With thionyl chloride; In dichloromethane; toluene; 1.1: Wittig condensation;

DOI:10.3987/com-02-s(m)43

Reference yield:

(1'S,3R)-2,3-dihydro-3-hydroxy-1-(1'-phenylethyl)-1H-isoindol-1-one (503859-63-0) → [(S)-3-Oxo-2-((S)-1-phenyl-ethyl)-2,3-dihydro-1H-isoindol-1-yl]-acetyl chloride

Guidance literature:

Multi-step reaction with 2 steps

1.1: toluene / 12 h / Heating

1.2: aq. potassium carbonate / ethanol / 2 h / Heating

2.1: thionyl chloride / CH₂Cl₂ / 2 h / Heating

With thionyl chloride; In dichloromethane; toluene; 1.1: Wittig condensation;

DOI:10.3987/com-02-s(m)43

upstream raw materials:

2-((S)-1-phenylethyl)-isoindoline-1,3-dione