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

Base Information

Chemical Name:(3R,4S)-(+)-4-(tert-butyldiphenylsilyloxy)-6-methoxy-N-methyl-3-phenyl-1,2,3,4-tetrahydroisoquinoline
CAS No.:208345-58-8
Molecular Formula:C₃₃H₃₇NO₂Si
Molecular Weight:507.748
Hs Code.:

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

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

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

There total 11 articles about (3R,4S)-(+)-4-(tert-butyldiphenylsilyloxy)-6-methoxy-N-methyl-3-phenyl-1,2,3,4-tetrahydroisoquinoline 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: 98.0%

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

: 208345-58-8
(3R,4S)-(+)-4-(tert-butyldiphenylsilyloxy)-6-methoxy-N-methyl-3-phenyl-1,2,3,4-tetrahydroisoquinoline

Guidance literature:: With dimethylsulfide borane complex; In tetrahydrofuran; for 5h; Heating;
DOI:10.1021/jo991119x

Reference yield:

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

: 208345-58-8
(3R,4S)-(+)-4-(tert-butyldiphenylsilyloxy)-6-methoxy-N-methyl-3-phenyl-1,2,3,4-tetrahydroisoquinoline

Guidance literature:: Multi-step reaction with 7 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

7: 98 percent / BH₃*DMS / tetrahydrofuran / 5 h / Heating

With 1H-imidazole; dimethylsulfide borane complex; (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 / 7: Reduction;
DOI:10.1021/jo991119x

Reference yield:

: 208345-54-4
(-)-(S)-6-methoxy-3-phenyl-3,4-dihydroisoquinolin-1(2H)-one

: 208345-58-8
(3R,4S)-(+)-4-(tert-butyldiphenylsilyloxy)-6-methoxy-N-methyl-3-phenyl-1,2,3,4-tetrahydroisoquinoline

Guidance literature:: Multi-step reaction with 4 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

4: 98 percent / BH₃*DMS / tetrahydrofuran / 5 h / Heating

With 1H-imidazole; dimethylsulfide borane complex; (camphorylsulfonyl)oxaziridine; sodium hydride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; 1: Methylation / 2: Oxidation / 3: Substitution / 4: Reduction;
DOI:10.1021/jo991119x