(S)-2-(4-benzyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-yl)-1-(p-tolyl)ethanone

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Chemical Name:(S)-2-(4-benzyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-yl)-1-(p-tolyl)ethanone
CAS No.:1450761-02-0
Molecular Formula:C₂₄H₂₃NO₂
Molecular Weight:357.452
Hs Code.:

Synonyms:

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Chemical Property of (S)-2-(4-benzyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-yl)-1-(p-tolyl)ethanone

Chemical Property:

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Technology Process of (S)-2-(4-benzyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-yl)-1-(p-tolyl)ethanone

There total 4 articles about (S)-2-(4-benzyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-yl)-1-(p-tolyl)ethanone 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:

: 19832-78-1
1-(4-methylphenyl)prop-2-en-1-one

: 1450761-14-4
2-(allyl(benzyl)amino)phenol

: 1450761-02-0
(S)-2-(4-benzyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-yl)-1-(p-tolyl)ethanone

: (R)-2-(4-benzyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-yl)-1-(p-tolyl)ethanone

Guidance literature:: With Hoveyda-Grubbs catalyst second generation; (S)-3,3'-bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; In dichloromethane; at 40 ℃; for 10h; Overall yield = 54%; enantioselective reaction; Inert atmosphere;
DOI:10.1039/c3cc43937b

Reference yield:

: 121025-48-7
C₁₉H₂₅NOSi

: 1450761-02-0
(S)-2-(4-benzyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-yl)-1-(p-tolyl)ethanone

: (R)-2-(4-benzyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-yl)-1-(p-tolyl)ethanone

Guidance literature:: Multi-step reaction with 4 steps

1: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C / Inert atmosphere

2: N-ethyl-N,N-diisopropylamine / acetonitrile / 60 °C / Inert atmosphere

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere

4: (S)-3,3'-bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; Hoveyda-Grubbs catalyst second generation / dichloromethane / 10 h / 40 °C / Inert atmosphere

With sodium tetrahydroborate; Hoveyda-Grubbs catalyst second generation; (S)-3,3'-bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 4: |Michael Addition;
DOI:10.1039/c3cc43937b

Reference yield:

: 95-55-6
2-amino-phenol

: 1450761-02-0
(S)-2-(4-benzyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-yl)-1-(p-tolyl)ethanone

: (R)-2-(4-benzyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-yl)-1-(p-tolyl)ethanone

Guidance literature:: Multi-step reaction with 6 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

2: magnesium sulfate / methanol / 3 h / Inert atmosphere; Reflux

3: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C / Inert atmosphere

4: N-ethyl-N,N-diisopropylamine / acetonitrile / 60 °C / Inert atmosphere

5: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere

6: (S)-3,3'-bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; Hoveyda-Grubbs catalyst second generation / dichloromethane / 10 h / 40 °C / Inert atmosphere

With 1H-imidazole; sodium tetrahydroborate; Hoveyda-Grubbs catalyst second generation; (S)-3,3'-bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; tetrabutyl ammonium fluoride; magnesium sulfate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 6: |Michael Addition;
DOI:10.1039/c3cc43937b