(R)-N-[1-(tert-butyldiphenylsilanyloxymethyl)-8-methoxy-3-oxo-2-propenyl-1,2,3,4-tetrahydroisoquinolin-7-yl]acetamide

Base Information

Chemical Name:(R)-N-[1-(tert-butyldiphenylsilanyloxymethyl)-8-methoxy-3-oxo-2-propenyl-1,2,3,4-tetrahydroisoquinolin-7-yl]acetamide
CAS No.:340963-70-4
Molecular Formula:C₃₂H₃₈N₂O₄Si
Molecular Weight:542.75
Hs Code.:

Synonyms:(R)-N-[1-(tert-butyldiphenylsilanyloxymethyl)-8-methoxy-3-oxo-2-propenyl-1,2,3,4-tetrahydroisoquinolin-7-yl]acetamide

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Chemical Property of (R)-N-[1-(tert-butyldiphenylsilanyloxymethyl)-8-methoxy-3-oxo-2-propenyl-1,2,3,4-tetrahydroisoquinolin-7-yl]acetamide

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Technology Process of (R)-N-[1-(tert-butyldiphenylsilanyloxymethyl)-8-methoxy-3-oxo-2-propenyl-1,2,3,4-tetrahydroisoquinolin-7-yl]acetamide

There total 17 articles about (R)-N-[1-(tert-butyldiphenylsilanyloxymethyl)-8-methoxy-3-oxo-2-propenyl-1,2,3,4-tetrahydroisoquinolin-7-yl]acetamide 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: 74.0%

: 340963-68-0
(R)-N-[2-allyl-1-(tert-butyldiphenylsilanyloxymethyl)-8-methoxy-3-oxo-1,2,3,4-tetrahydroisoquinolin-7-yl]acetamide

: 340963-70-4
(R)-N-[1-(tert-butyldiphenylsilanyloxymethyl)-8-methoxy-3-oxo-2-propenyl-1,2,3,4-tetrahydroisoquinolin-7-yl]acetamide

Guidance literature:: Wilkinson's catalyst; In toluene; for 14h; Heating;
DOI:10.1021/jo015512q

Reference yield:

: 82807-38-3
1-(2-methoxyphenyl)ethane-1,2-diol

: 340963-70-4
(R)-N-[1-(tert-butyldiphenylsilanyloxymethyl)-8-methoxy-3-oxo-2-propenyl-1,2,3,4-tetrahydroisoquinolin-7-yl]acetamide

Guidance literature:: Multi-step reaction with 16 steps

1: 94 percent / pyridine / 8 h / 20 °C

2: 83 percent / KNO₃; TFAA / CHCl₃ / 48 h / 0 °C

3: 93 percent / K₂CO₃ / methanol; H₂O / 0.5 h

4: 73 percent / imidazole / dimethylformamide / 4 h / 20 °C

5: 89 percent / PPh₃; DEAD / tetrahydrofuran / 1.5 h

6: 100 percent / NH₂NH₂*H₂O / ethanol / 3 h / Heating

7: 78 percent / 4 Angstroem MS; CsOH*H₂O / dimethylformamide

8: 86 percent / Et₃N / diethyl ether / 0 - 20 °C

9: 76 percent / ethyl viologen dibromide; K₂CO₃; Na₂S₂O₄ / CH₂Cl₂; H₂O / 24 h

10: 402.1 mg / Et₃N / CH₂Cl₂ / 12 h / 20 °C

11: 94 percent / K₂CO₃ / H₂O; methanol / 2 h

12: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -50 - 20 °C

13: 1.269 g / p-TsOH / dioxane / 1.5 h / Heating

14: 181.3 mg / DMAP; pyridine / CH₂Cl₂ / 17 h / 20 °C

15: 76.4 mg / AIBN; Bu₃SnH / benzene / 60 h

16: 74 percent / ClRh(PPh₃)3 / toluene / 14 h / Heating

With pyridine; 1H-imidazole; dmap; cesium hydroxide; sodium dithionite; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); 4 Angstroem MS; tri-n-butyl-tin hydride; potassium carbonate; toluene-4-sulfonic acid; hydrazine hydrate; dimethyl sulfoxide; potassium nitrate; triethylamine; triphenylphosphine; 1,1′-diethyl-[4,4′-bipyridine]-1,1′-diium dibromide; trifluoroacetic anhydride; diethylazodicarboxylate; Wilkinson's catalyst; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; diethyl ether; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene; benzene; 5: Mitsunobu reaction / 12: Swern oxidation;
DOI:10.1021/jo015512q

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 340963-70-4
(R)-N-[1-(tert-butyldiphenylsilanyloxymethyl)-8-methoxy-3-oxo-2-propenyl-1,2,3,4-tetrahydroisoquinolin-7-yl]acetamide

Guidance literature:: Multi-step reaction with 13 steps

1: 73 percent / imidazole / dimethylformamide / 4 h / 20 °C

2: 89 percent / PPh₃; DEAD / tetrahydrofuran / 1.5 h

3: 100 percent / NH₂NH₂*H₂O / ethanol / 3 h / Heating

4: 78 percent / 4 Angstroem MS; CsOH*H₂O / dimethylformamide

5: 86 percent / Et₃N / diethyl ether / 0 - 20 °C

6: 76 percent / ethyl viologen dibromide; K₂CO₃; Na₂S₂O₄ / CH₂Cl₂; H₂O / 24 h

7: 402.1 mg / Et₃N / CH₂Cl₂ / 12 h / 20 °C

8: 94 percent / K₂CO₃ / H₂O; methanol / 2 h

9: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -50 - 20 °C

10: 1.269 g / p-TsOH / dioxane / 1.5 h / Heating

11: 181.3 mg / DMAP; pyridine / CH₂Cl₂ / 17 h / 20 °C

12: 76.4 mg / AIBN; Bu₃SnH / benzene / 60 h

13: 74 percent / ClRh(PPh₃)3 / toluene / 14 h / Heating

With pyridine; 1H-imidazole; dmap; cesium hydroxide; sodium dithionite; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); 4 Angstroem MS; tri-n-butyl-tin hydride; potassium carbonate; toluene-4-sulfonic acid; hydrazine hydrate; dimethyl sulfoxide; triethylamine; triphenylphosphine; 1,1′-diethyl-[4,4′-bipyridine]-1,1′-diium dibromide; diethylazodicarboxylate; Wilkinson's catalyst; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene; 2: Mitsunobu reaction / 9: Swern oxidation;
DOI:10.1021/jo015512q