(3R,5R)-5-(hydroxymethyl)-2-phenylisoxazolidine-3-carbonitrile

Base Information

• Chemical Name: (3R,5R)-5-(hydroxymethyl)-2-phenylisoxazolidine-3-carbonitrile
• CAS No.: 192506-15-3
• Molecular Formula: C₁₁H₁₂N₂O₂
• Molecular Weight: 204.228
• Mol file: 192506-15-3.mol

Synonyms:(3R,5R)-5-(hydroxymethyl)-2-phenylisoxazolidine-3-carbonitrile

Chemical Property of (3R,5R)-5-(hydroxymethyl)-2-phenylisoxazolidine-3-carbonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (3R,5R)-5-(hydroxymethyl)-2-phenylisoxazolidine-3-carbonitrile

There total 2 articles about (3R,5R)-5-(hydroxymethyl)-2-phenylisoxazolidine-3-carbonitrile 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:

allyl alcohol (107-18-6) + N-(cyanomethylene)aniline N-oxide (192506-11-9) → (3S,5S)-5-(hydroxymethyl)-2-phenylisoxazolidine-3-carbonitrile + (3R,5R)-5-(hydroxymethyl)-2-phenylisoxazolidine-3-carbonitrile (192506-15-3)

Guidance literature:

With L-(+)-diisopropyl tartrate; diethylzinc; ethylzinc chloride; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 2.) CHCl₃, 45 deg C, 52 h;

DOI:10.1246/cl.1997.547

Reference yield:

allyl alcohol (107-18-6) + N-(cyanomethylene)aniline N-oxide (192506-11-9) → (3S,5S)-5-(hydroxymethyl)-2-phenylisoxazolidine-3-carbonitrile + (3S,5R)-5-Hydroxymethyl-2-phenyl-isoxazolidine-3-carbonitrile + (3R,5S)-5-Hydroxymethyl-2-phenyl-isoxazolidine-3-carbonitrile + (3R,5R)-5-(hydroxymethyl)-2-phenylisoxazolidine-3-carbonitrile (192506-15-3)

Guidance literature:

With L-(+)-diisopropyl tartrate; diethylzinc; ethylzinc chloride; Product distribution; multistep reaction; 2.) CHCl₃, 0 deg C, 43 h; various reaction parameters; ee investigated;

DOI:10.1246/cl.1997.547

Reference yield: 86.0%

(3R,5R)-5-(hydroxymethyl)-2-phenylisoxazolidine-3-carbonitrile (192506-15-3) → (2R,4R)-4,5-dihydroxy-2-(phenylamino)pentanonitrile

Guidance literature:

With hydrogen; palladium on activated charcoal;

DOI:10.1246/cl.1997.547

upstream raw materials:

allyl alcohol

N-(cyanomethylene)aniline N-oxide