(2S,3R)-3-hydroxy-N-methoxy-N,2-dimethylpentanamide

Base Information

• Chemical Name: (2S,3R)-3-hydroxy-N-methoxy-N,2-dimethylpentanamide
• CAS No.: 145937-04-8
• Molecular Formula: C₈H₁₇NO₃
• Molecular Weight: 175.228
• Mol file: 145937-04-8.mol

Synonyms:(2S,3R)-3-hydroxy-N-methoxy-N,2-dimethylpentanamide

Chemical Property of (2S,3R)-3-hydroxy-N-methoxy-N,2-dimethylpentanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-3-hydroxy-N-methoxy-N,2-dimethylpentanamide

There total 1 articles about (2S,3R)-3-hydroxy-N-methoxy-N,2-dimethylpentanamide 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:

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + (4S,2'S,3'R)-3-(2'-methyl-3'-hydroxypentanoyl)-4-benzyl-2-oxazolidinone (124356-91-8) → (S)-4-Benzyl-2-oxazolidinone (90719-32-7) + (2S,3R)-3-hydroxy-N-methoxy-N,2-dimethylpentanamide (145937-04-8)

Guidance literature:

With trimethylaluminum; Yield given. Multistep reaction. Yields of byproduct given; 1) CH2Cl2, toluene, rt, 1 h; 2) CH2Cl2, toluene, -20 deg C --> rt, rt, 1.5 h;

DOI:10.1021/jo9809433

Reference yield:

(2S,3R)-3-hydroxy-N-methoxy-N,2-dimethylpentanamide (145937-04-8) → (2R,3S,4S,6R)-7-Hydroxy-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-heptanoic acid (E)-(1R,2R)-1-ethyl-4-iodo-2-methyl-but-3-enyl ester (216493-97-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 76 percent / imidazole / dimethylformamide / 24 h / Ambient temperature

2: 78 percent / DIBAL-H / toluene / 1.5 h / -78 °C

3: 59 percent / CrCl₂ / tetrahydrofuran / 1.5 h / 0 °C

4: 94 percent / aq. HF / acetonitrile / 4 h / Ambient temperature

5: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) DMAP / 1) THF, rt, 2 h; 2) benzene, rt, 24 h

6: 94 percent / aq. HF / acetonitrile / Ambient temperature

With 1H-imidazole; chromium dichloride; dmap; 2,4,6-trichlorobenzoyl chloride; hydrogen fluoride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/jo9809433

Reference yield:

(2S,3R)-3-hydroxy-N-methoxy-N,2-dimethylpentanamide (145937-04-8) → (2R,3S,4S,6R)-3-(4-Methoxy-benzyloxy)-2,4,6-trimethyl-7-oxo-heptanoic acid (E)-(1R,2R)-1-ethyl-4-iodo-2-methyl-but-3-enyl ester (216493-93-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 76 percent / imidazole / dimethylformamide / 24 h / Ambient temperature

2: 78 percent / DIBAL-H / toluene / 1.5 h / -78 °C

3: 59 percent / CrCl₂ / tetrahydrofuran / 1.5 h / 0 °C

4: 94 percent / aq. HF / acetonitrile / 4 h / Ambient temperature

5: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) DMAP / 1) THF, rt, 2 h; 2) benzene, rt, 24 h

6: 94 percent / aq. HF / acetonitrile / Ambient temperature

7: Dess-Martin periodinane, pyridine / CH₂Cl₂ / 8 h / Ambient temperature

With pyridine; 1H-imidazole; chromium dichloride; dmap; 2,4,6-trichlorobenzoyl chloride; hydrogen fluoride; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/jo9809433

upstream raw materials:

N,O-dimethylhydroxylamine*hydrochloride

(4S,2'S,3'R)-3-(2'-methyl-3'-hydroxypentanoyl)-4-benzyl-2-oxazolidinone

Downstream raw materials:

(R)-4-Benzyl-3-[(2R,3S,4R,5R)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-heptanoyl]-oxazolidin-2-one

(S)-4-Benzyl-3-[(2S,3R,4R,5R)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-heptanoyl]-oxazolidin-2-one

(2R,3S,4S,6R)-7-Hydroxy-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-heptanoic acid (E)-(1R,2R)-1-ethyl-4-iodo-2-methyl-but-3-enyl ester

(2R,3S,4S,6R)-3-(4-Methoxy-benzyloxy)-2,4,6-trimethyl-7-oxo-heptanoic acid (E)-(1R,2R)-1-ethyl-4-iodo-2-methyl-but-3-enyl ester