[2R,3S,1'S,2'S]-(+)-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxy-N,2-dimethyl-butanamide

Base Information

• Chemical Name: [2R,3S,1'S,2'S]-(+)-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxy-N,2-dimethyl-butanamide
• CAS No.: 219783-12-7
• Molecular Formula: C₁₅H₂₃NO₃
• Molecular Weight: 265.353

Synonyms:[2R,3S,1'S,2'S]-(+)-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxy-N,2-dimethyl-butanamide

Chemical Property of [2R,3S,1'S,2'S]-(+)-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxy-N,2-dimethyl-butanamide

Chemical Property:

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Technology Process of [2R,3S,1'S,2'S]-(+)-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxy-N,2-dimethyl-butanamide

There total 2 articles about [2R,3S,1'S,2'S]-(+)-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxy-N,2-dimethyl-butanamide 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: 88.0%

acetaldehyde (75-07-0,9002-91-9) + N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpropionamide (159213-03-3) → [2R,3S,1'S,2'S]-(+)-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxy-N,2-dimethyl-butanamide (219783-12-7) + (2R,3R)-3-Hydroxy-N-((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-2,N-dimethyl-butyramide

Guidance literature:

N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpropionamide; With lithium diisopropyl amide; In tetrahydrofuran; at -78 - 20 ℃;

With zirconocene dichloride; In tetrahydrofuran; at -78 ℃; for 1h;

acetaldehyde; In tetrahydrofuran; at -105 ℃; for 2.33333h;

DOI:10.1021/jo000035h

Reference yield:

acetaldehyde (75-07-0,9002-91-9) + N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpropionamide (159213-03-3) → [2R,3S,1'S,2'S]-(+)-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxy-N,2-dimethyl-butanamide (219783-12-7) + (2R,3R)-3-Hydroxy-N-((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-2,N-dimethyl-butyramide + (2S,3S)-3-Hydroxy-N-((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-2,N-dimethyl-butyramide

Guidance literature:

With zirconocene dichloride; lithium diisopropyl amide; Yield given; Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) THF, -78 deg C, 1 h then RT; 2.) THF, -78 deg C, 1 h; -105 deg C, 20 min; -78 deg C, 2 h;

DOI:10.1016/S0040-4039(98)02082-6

Reference yield: 93.0%

[2R,3S,1'S,2'S]-(+)-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxy-N,2-dimethyl-butanamide (219783-12-7) → pseudoephedrine (90-82-4,7009-81-6,90-83-5,6912-63-6) + syn-2,3-3-hydroxy-2-methyl-butanoic acid (66729-02-0)

Guidance literature:

With sulfuric acid; In 1,4-dioxane; for 2h; Heating;

DOI:10.1021/jo000035h

upstream raw materials:

acetaldehyde

N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpropionamide

Downstream raw materials:

[2R,3S]-(+)-hydroxy-2-methyl-1-phenyl-1-butanone

pseudoephedrine

syn-2,3-3-hydroxy-2-methyl-butanoic acid

[1S,2R,3S]-(+)-2-methyl-1-phenyl-1,3-butanediol

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