(αR,5S,6S)-N-(α-methylbenzyl)-6-difluoromethyl-5-hydroxy-5,6-dihydro-4-pyridone

Base Information

• Chemical Name: (αR,5S,6S)-N-(α-methylbenzyl)-6-difluoromethyl-5-hydroxy-5,6-dihydro-4-pyridone
• CAS No.: 161665-02-7
• Molecular Formula: C₁₄H₁₅F₂NO₂
• Molecular Weight: 267.275
• Mol file: 161665-02-7.mol

Synonyms:(αR,5S,6S)-N-(α-methylbenzyl)-6-difluoromethyl-5-hydroxy-5,6-dihydro-4-pyridone

Chemical Property of (αR,5S,6S)-N-(α-methylbenzyl)-6-difluoromethyl-5-hydroxy-5,6-dihydro-4-pyridone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (αR,5S,6S)-N-(α-methylbenzyl)-6-difluoromethyl-5-hydroxy-5,6-dihydro-4-pyridone

There total 1 articles about (αR,5S,6S)-N-(α-methylbenzyl)-6-difluoromethyl-5-hydroxy-5,6-dihydro-4-pyridone 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:

(αR,6S)-N-(α-methylbenzyl)-6-difluoromethyl-5,6-dihydro-4-pyridone (156978-54-0) → (αR,5S,6S)-N-(α-methylbenzyl)-6-difluoromethyl-5-hydroxy-5,6-dihydro-4-pyridone (161665-02-7)

Guidance literature:

With N-phenylsulfonyl-2-phenyloxazolidine; sodium hexamethyldisilazane; toluene-4-sulfonic acid; Yield given. Multistep reaction;

DOI:10.1016/0957-4166(94)80053-7

Reference yield: 99.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (αR,5S,6S)-N-(α-methylbenzyl)-6-difluoromethyl-5-hydroxy-5,6-dihydro-4-pyridone (161665-02-7) → (αR,5S,6S)-N-(α-methylbenzyl)-6-difluoromethyl-5-<(tert-butyldimethylsilyl)oxy>-5,6-dihydro-4-pyridone (161665-04-9)

Guidance literature:

With 1H-imidazole; In dichloromethane; for 0.5h; Ambient temperature;

DOI:10.1016/0957-4166(94)80053-7

Reference yield:

(αR,5S,6S)-N-(α-methylbenzyl)-6-difluoromethyl-5-hydroxy-5,6-dihydro-4-pyridone (161665-02-7) → (αR,3S,4R,5S,6S)-N-(α-methylbenzyl)-6-difluoromethyl-3,4,5-trihydroxypiperidine

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / imidazole / CH₂Cl₂ / 0.5 h / Ambient temperature

2: 1.) BH₃*THF, 2.) 10percent aq. NaOH, 35percent aq. H₂O₂ / 1.) THF, RT, 2 h, 2.) THF, RT, 1 h

3: 70 percent / 3 N HCl / methanol / 24 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; sodium hydroxide; borane-THF; dihydrogen peroxide; In methanol; dichloromethane;

DOI:10.1016/0957-4166(94)80053-7

upstream raw materials:

(αR,6S)-N-(α-methylbenzyl)-6-difluoromethyl-5,6-dihydro-4-pyridone

Downstream raw materials:

(αR,5S,6S)-N-(α-methylbenzyl)-6-difluoromethyl-5-<(tert-butyldimethylsilyl)oxy>-5,6-dihydro-4-pyridone

(αR,3S,4S,5S,6S)-N-(α-methylbenzyl)-6-difluoromethyl-5-<(tert-butyldimethylsilyl)oxy>-3,4-dihydroxypiperidine