(2S,4S,9aS)-4-[3-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-octahydro-quinolizin-2-ol

Base Information

Chemical Name:(2S,4S,9aS)-4-[3-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-octahydro-quinolizin-2-ol
CAS No.:851755-98-1
Molecular Formula:C₂₂H₃₇NO₃Si
Molecular Weight:391.626
Hs Code.:

Synonyms:(2S,4S,9aS)-4-[3-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-octahydro-quinolizin-2-ol

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Chemical Property of (2S,4S,9aS)-4-[3-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-octahydro-quinolizin-2-ol

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Technology Process of (2S,4S,9aS)-4-[3-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-octahydro-quinolizin-2-ol

There total 14 articles about (2S,4S,9aS)-4-[3-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-octahydro-quinolizin-2-ol 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: 83.0%

: 851755-97-0
(4S,9aS)-4-(3-(tert-butyldimethylsilyloxy)-4-methoxyphenyl)hexahydro-1H-quinolizin-2(6H)-one

: 851755-98-1
(2S,4S,9aS)-4-[3-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-octahydro-quinolizin-2-ol

Guidance literature:: With lithium tri-sec-butyl(hydrido)borate; In tetrahydrofuran; at -78 ℃;
DOI:10.1016/j.tetlet.2005.02.110

Reference yield:

: 851755-89-0
(S)-1-(3-Benzyloxy-4-methoxy-phenyl)-but-3-enylamine

: 851755-98-1
(2S,4S,9aS)-4-[3-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-octahydro-quinolizin-2-ol

Guidance literature:: Multi-step reaction with 11 steps

1: 87 percent / toluene / Heating

2: 86 percent / O₂ / PdCl₂; CuCl₂ / H₂O; dimethylformamide / 85 °C

3: TsOH / benzene / Heating

4: (NH₂)2*H₂O / ethanol / Heating

5: 100 percent / CHCl₃ / 20 °C

6: 88 percent / TiCl₄ / CH₂Cl₂ / 0 °C

7: 93 percent / H₂ / Pd/C / methanol; tetrahydrofuran

8: 76 percent / CBr₄; Ph₃P / CH₂Cl₂; triethylamine / 20 °C

9: HCl / tetrahydrofuran / Heating

10: pyridine / 0 °C

11: 83 percent / LS-Selectride(R) / tetrahydrofuran / -78 °C

With hydrogenchloride; carbon tetrabromide; hydrogen; oxygen; titanium tetrachloride; toluene-4-sulfonic acid; hydrazine hydrate; lithium tri-sec-butyl(hydrido)borate; triphenylphosphine; palladium on activated charcoal; copper dichloride; palladium dichloride; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; chloroform; water; triethylamine; N,N-dimethyl-formamide; toluene; benzene; 2: Wacker oxidation / 6: Mannich-type cyclization;
DOI:10.1016/j.tetlet.2005.02.110

Reference yield:

: 851755-92-5
(S)-1-(3-Benzyloxy-4-methoxy-phenyl)-2-(2-methyl-[1,3]dioxolan-2-yl)-ethylamine

: 851755-98-1
(2S,4S,9aS)-4-[3-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-octahydro-quinolizin-2-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / CHCl₃ / 20 °C

2: 88 percent / TiCl₄ / CH₂Cl₂ / 0 °C

3: 93 percent / H₂ / Pd/C / methanol; tetrahydrofuran

4: 76 percent / CBr₄; Ph₃P / CH₂Cl₂; triethylamine / 20 °C

5: HCl / tetrahydrofuran / Heating

6: pyridine / 0 °C

7: 83 percent / LS-Selectride(R) / tetrahydrofuran / -78 °C

With hydrogenchloride; carbon tetrabromide; hydrogen; titanium tetrachloride; lithium tri-sec-butyl(hydrido)borate; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; chloroform; triethylamine; 2: Mannich-type cyclization;
DOI:10.1016/j.tetlet.2005.02.110