(3R,4S)-(+)-4-hydroxy-6-methoxy-N-methyl-3-phenyl-3,4-dihydro-1(2H)-isoquinolone

Base Information

Chemical Name:(3R,4S)-(+)-4-hydroxy-6-methoxy-N-methyl-3-phenyl-3,4-dihydro-1(2H)-isoquinolone
CAS No.:208345-56-6
Molecular Formula:C₁₇H₁₇NO₃
Molecular Weight:283.327
Hs Code.:

Synonyms:(3R,4S)-(+)-4-hydroxy-6-methoxy-N-methyl-3-phenyl-3,4-dihydro-1(2H)-isoquinolone

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Chemical Property of (3R,4S)-(+)-4-hydroxy-6-methoxy-N-methyl-3-phenyl-3,4-dihydro-1(2H)-isoquinolone

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Technology Process of (3R,4S)-(+)-4-hydroxy-6-methoxy-N-methyl-3-phenyl-3,4-dihydro-1(2H)-isoquinolone

There total 8 articles about (3R,4S)-(+)-4-hydroxy-6-methoxy-N-methyl-3-phenyl-3,4-dihydro-1(2H)-isoquinolone 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: 85.0%

: 208345-55-5
(3S)-(-)-6-methoxy-N-methyl-3-phenyl-3,4-dihydro-1(2H)-isoquinolone

: 208345-56-6
(3R,4S)-(+)-4-hydroxy-6-methoxy-N-methyl-3-phenyl-3,4-dihydro-1(2H)-isoquinolone

Guidance literature:: With (-)-(camphorylsulfonyl)oxaziridine; lithium diisopropyl amide;
DOI:10.1016/S0040-4039(98)00506-1

Reference yield:

: 90359-73-2
N,N-diethyl-4-methoxy-2-methylbenzamide

: 208345-56-6
(3R,4S)-(+)-4-hydroxy-6-methoxy-N-methyl-3-phenyl-3,4-dihydro-1(2H)-isoquinolone

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / LDA / tetrahydrofuran; cyclohexane / 0.25 h / -78 °C

2: 99 percent / TFA / methanol / 2 h / 0 °C

3: 96 percent / t-BuLi / tetrahydrofuran; pentane / 0.5 h / -78 °C

4: 95 percent / NaH / tetrahydrofuran / 1 h / 20 °C

5: 85 percent / (camphorylsulfonyl)oxaziridine; LDA / tetrahydrofuran / 0.33 h / -78 °C

With (camphorylsulfonyl)oxaziridine; tert.-butyl lithium; sodium hydride; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; cyclohexane; pentane; 1: Addition / 2: Hydrolysis / 3: Cyclization / 4: Methylation / 5: Oxidation;
DOI:10.1021/jo991119x

Reference yield:

: 208345-53-3
(S)-(-)-N,N-diethyl-4-methoxy-2-(2-amino-2-phenylethyl)benzamide

: 208345-56-6
(3R,4S)-(+)-4-hydroxy-6-methoxy-N-methyl-3-phenyl-3,4-dihydro-1(2H)-isoquinolone

Guidance literature:: Multi-step reaction with 3 steps

1: 96 percent / t-BuLi / tetrahydrofuran; pentane / 0.5 h / -78 °C

2: 95 percent / NaH / tetrahydrofuran / 1 h / 20 °C

3: 85 percent / (camphorylsulfonyl)oxaziridine; LDA / tetrahydrofuran / 0.33 h / -78 °C

With (camphorylsulfonyl)oxaziridine; tert.-butyl lithium; sodium hydride; lithium diisopropyl amide; In tetrahydrofuran; pentane; 1: Cyclization / 2: Methylation / 3: Oxidation;
DOI:10.1021/jo991119x