(2S,6S)-1,6-dihydro-6-hydroxy-2-methyl-N-tosylpyridin-3(2H)-one

Base Information

• Chemical Name: (2S,6S)-1,6-dihydro-6-hydroxy-2-methyl-N-tosylpyridin-3(2H)-one
• CAS No.: 148346-42-3
• Molecular Formula: C₁₃H₁₅NO₄S
• Molecular Weight: 281.332
• Mol file: 148346-42-3.mol

Synonyms:(2S,6S)-1,6-dihydro-6-hydroxy-2-methyl-N-tosylpyridin-3(2H)-one

Chemical Property of (2S,6S)-1,6-dihydro-6-hydroxy-2-methyl-N-tosylpyridin-3(2H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,6S)-1,6-dihydro-6-hydroxy-2-methyl-N-tosylpyridin-3(2H)-one

There total 3 articles about (2S,6S)-1,6-dihydro-6-hydroxy-2-methyl-N-tosylpyridin-3(2H)-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: 94.6%

(S)-N-tosyl-α'-methyl-α-furfuryl amine (134452-27-0) → (2S,6S)-1,6-dihydro-6-hydroxy-2-methyl-N-tosylpyridin-3(2H)-one (148346-42-3)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 30 ℃; for 1h;

Reference yield: 8.0%

N-(1-furan-2-yl-ethyl)-4-methyl-benzenesulfonamide (134340-62-8) → (R)-6-Hydroxy-2-methyl-1-(toluene-4-sulfonyl)-1,6-dihydro-2H-pyridin-3-one (134340-68-4,148346-40-1,148346-42-3) + (R)-N-(1-(furan-2-yl)ethyl)-4-methyl-benzenesulfonamide (158568-75-3) + (S)-N-tosyl-α'-methyl-α-furfuryl amine (134452-27-0)

Guidance literature:

With titanium(IV) isopropylate; tert.-butylhydroperoxide; calcium hydride; L-(+)-diisopropyl tartrate; silica gel; In dichloromethane; for 48h; Yields of byproduct given; Ambient temperature;

DOI:10.1016/0040-4039(91)80360-I

Reference yield:

(E)-N-(furan-2-ylmethylene)-4-methylbenzenesulfonamide (135822-87-6) → (R)-6-Hydroxy-2-methyl-1-(toluene-4-sulfonyl)-1,6-dihydro-2H-pyridin-3-one (134340-68-4,148346-40-1,148346-42-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / -70 °C

2: 8 percent / Ti(OiPr)4, L-(+)-DIPT, TBHP, CaH₂, silica gel / CH₂Cl₂ / 48 h / Ambient temperature

With titanium(IV) isopropylate; tert.-butylhydroperoxide; calcium hydride; L-(+)-diisopropyl tartrate; silica gel; In dichloromethane;

DOI:10.1016/0040-4039(91)80360-I

upstream raw materials:

N-(1-furan-2-yl-ethyl)-4-methyl-benzenesulfonamide

(E)-N-(furan-2-ylmethylene)-4-methylbenzenesulfonamide

(S)-N-tosyl-α'-methyl-α-furfuryl amine

Downstream raw materials:

S-methyl O-<(2S,3R,6R)-2-methyl-6-propyl-N-tosylpiperidin-3-yl> dithiocarbonate

(2S,3R,6S)-6-allyl-2-methyl-N-tosylpiperidin-3-ol

(2S,3R,6S)-6-ethoxy-2-methyl-N-tosylpiperidin-3-ol

(2S,3R,6R)-2-methyl-6-propyl-N-tosylpiperidin-3-ol