(3S)-3-[(2R)-2-hydroxy-2-(4-methylphenyl)ethyl]-2,3-dihydro-1H-isoindol-1-one

Base Information

• Chemical Name: (3S)-3-[(2R)-2-hydroxy-2-(4-methylphenyl)ethyl]-2,3-dihydro-1H-isoindol-1-one
• CAS No.: 944052-62-4
• Molecular Formula: C₁₇H₁₇NO₂
• Molecular Weight: 267.327
• Mol file: 944052-62-4.mol

Synonyms:(3S)-3-[(2R)-2-hydroxy-2-(4-methylphenyl)ethyl]-2,3-dihydro-1H-isoindol-1-one

Chemical Property of (3S)-3-[(2R)-2-hydroxy-2-(4-methylphenyl)ethyl]-2,3-dihydro-1H-isoindol-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S)-3-[(2R)-2-hydroxy-2-(4-methylphenyl)ethyl]-2,3-dihydro-1H-isoindol-1-one

There total 4 articles about (3S)-3-[(2R)-2-hydroxy-2-(4-methylphenyl)ethyl]-2,3-dihydro-1H-isoindol-1-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: 66.0%

(3S)-3-[(2R)-2-hydroxy-2-(4-methylphenyl)ethyl]-2-[(1S,5R)-5,8,8-trimethyl-2-oxo-3-oxabicyclo[3.2.1]octane-1-carbonyl]-2,3-dihydroisoindol-1-one (944052-56-6) → (3S)-3-[(2R)-2-hydroxy-2-(4-methylphenyl)ethyl]-2,3-dihydro-1H-isoindol-1-one (944052-62-4)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1002/jhet.5570440312

Reference yield:

C17H16INO2 → (3S)-3-[(2R)-2-hydroxy-2-(4-methylphenyl)ethyl]-2,3-dihydro-1H-isoindol-1-one (944052-62-4)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / dimethyl sulfoxide / 3 h / 80 °C / Inert atmosphere

2: lithium hydroxide / water; ethanol; tetrahydrofuran / 3 h / 0 °C

With palladium diacetate; triethylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; lithium hydroxide; In tetrahydrofuran; ethanol; water; dimethyl sulfoxide;

DOI:10.1021/jacs.7b04795

Reference yield:

1-ethenyl-4-methylbenzene (622-97-9,24936-41-2) → (3S)-3-[(2R)-2-hydroxy-2-(4-methylphenyl)ethyl]-2,3-dihydro-1H-isoindol-1-one (944052-62-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: (R)-3,3'-di(4-tert-butylphenyl)(1,1'-binaphthyl)-2,2'-disulfonic acid; magnesium ethylate; potassium tert-butylate / monoethylene glycol diethyl ether / 0.5 h / 0 °C / Inert atmosphere; Molecular sieve

1.2: 5 h / 0 °C / Inert atmosphere; Molecular sieve

2.1: triethylamine; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / dimethyl sulfoxide / 3 h / 80 °C / Inert atmosphere

3.1: lithium hydroxide / water; ethanol; tetrahydrofuran / 3 h / 0 °C

With (R)-3,3'-di(4-tert-butylphenyl)(1,1'-binaphthyl)-2,2'-disulfonic acid; potassium tert-butylate; palladium diacetate; magnesium ethylate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; lithium hydroxide; In tetrahydrofuran; ethanol; monoethylene glycol diethyl ether; water; dimethyl sulfoxide;

DOI:10.1021/jacs.7b04795

upstream raw materials:

(3S)-3-[(2R)-2-hydroxy-2-(4-methylphenyl)ethyl]-2-[(1S,5R)-5,8,8-trimethyl-2-oxo-3-oxabicyclo[3.2.1]octane-1-carbonyl]-2,3-dihydroisoindol-1-one

1-ethenyl-4-methylbenzene

Downstream raw materials:

(3R,4aS)-3-(4-methylphenyl)-3,4,4a,9-tetrahydrooxazino[4,3-a]isoindole

{(1S)-2-[(1S)-3-oxo-2,3-dihydro-1H-isoindol-1-yl]-1-(4-methylphenyl)ethyl} benzoate

(3R,4aS)-3-(4-methylphenyl)-3,4,4a,9-tetrahydrooxazino[4,3-a]isoindol-1-one