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

Base Information

• Chemical Name: (3R,4S)-(+)-4-(tert-butyldiphenylsilyloxy)-6-methoxy-N-methyl-3-phenyl-3,4-dihydro-1(2H)-isoquinolone
• CAS No.: 208345-57-7
• Molecular Formula: C₃₃H₃₅NO₃Si
• Molecular Weight: 521.731
• Mol file: 208345-57-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about (3R,4S)-(+)-4-(tert-butyldiphenylsilyloxy)-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: 90.0%

tert-butylchlorodiphenylsilane (58479-61-1) + (3R,4S)-(+)-4-hydroxy-6-methoxy-N-methyl-3-phenyl-3,4-dihydro-1(2H)-isoquinolone (208345-56-6) → (3R,4S)-(+)-4-(tert-butyldiphenylsilyloxy)-6-methoxy-N-methyl-3-phenyl-3,4-dihydro-1(2H)-isoquinolone (208345-57-7)

Guidance literature:

With 1H-imidazole;

DOI:10.1016/S0040-4039(98)00506-1

Reference yield:

N,N-diethyl-4-methoxy-2-methylbenzamide (90359-73-2) → (3R,4S)-(+)-4-(tert-butyldiphenylsilyloxy)-6-methoxy-N-methyl-3-phenyl-3,4-dihydro-1(2H)-isoquinolone (208345-57-7)

Guidance literature:

Multi-step reaction with 6 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

6: 90 percent / imidazole / CH₂Cl₂ / 3 h / 20 °C

With 1H-imidazole; (camphorylsulfonyl)oxaziridine; tert.-butyl lithium; sodium hydride; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; pentane; 1: Addition / 2: Hydrolysis / 3: Cyclization / 4: Methylation / 5: Oxidation / 6: Substitution;

DOI:10.1021/jo991119x

Reference yield:

(-)-(S)-6-methoxy-3-phenyl-3,4-dihydroisoquinolin-1(2H)-one (208345-54-4) → (3R,4S)-(+)-4-(tert-butyldiphenylsilyloxy)-6-methoxy-N-methyl-3-phenyl-3,4-dihydro-1(2H)-isoquinolone (208345-57-7)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 85 percent / (camphorylsulfonyl)oxaziridine; LDA / tetrahydrofuran / 0.33 h / -78 °C

3: 90 percent / imidazole / CH₂Cl₂ / 3 h / 20 °C

With 1H-imidazole; (camphorylsulfonyl)oxaziridine; sodium hydride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; 1: Methylation / 2: Oxidation / 3: Substitution;

DOI:10.1021/jo991119x

upstream raw materials:

tert-butylchlorodiphenylsilane

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

N,N-diethyl-4-methoxy-2-methylbenzamide

(R,E)-N-benzylidene-4-methylbenzenesulfinamide

Downstream raw materials:

(3R,4S)-(+)-4-(tert-butyldiphenylsilyloxy)-6-methoxy-N-methyl-3-phenyl-1,2,3,4-tetrahydroisoquinoline