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

Base Information

• Chemical Name: (4S,9aS)-4-(3-(tert-butyldimethylsilyloxy)-4-methoxyphenyl)hexahydro-1H-quinolizin-2(6H)-one
• CAS No.: 851755-97-0
• Molecular Formula: C₂₂H₃₅NO₃Si
• Molecular Weight: 389.61

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

Chemical Property of (4S,9aS)-4-(3-(tert-butyldimethylsilyloxy)-4-methoxyphenyl)hexahydro-1H-quinolizin-2(6H)-one

Chemical Property:

Purity/Quality:

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Technology Process of (4S,9aS)-4-(3-(tert-butyldimethylsilyloxy)-4-methoxyphenyl)hexahydro-1H-quinolizin-2(6H)-one

There total 15 articles about (4S,9aS)-4-(3-(tert-butyldimethylsilyloxy)-4-methoxyphenyl)hexahydro-1H-quinolizin-2(6H)-one 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: 77.0%

(4S,9aS)-4-(3-hydroxy-4-methoxyphenyl)hexahydro-1H-quinolizin-2(6H)-one (33187-34-7,52656-93-6) + t-butyldimethylsiyl triflate (69739-34-0) → (4S,9aS)-4-(3-(tert-butyldimethylsilyloxy)-4-methoxyphenyl)hexahydro-1H-quinolizin-2(6H)-one (851755-97-0)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 2h; enantioselective reaction;

DOI:10.1021/acs.orglett.9b01840

Reference yield:

(S)-1-(3-Benzyloxy-4-methoxy-phenyl)-but-3-enylamine (851755-89-0) → (4S,9aS)-4-(3-(tert-butyldimethylsilyloxy)-4-methoxyphenyl)hexahydro-1H-quinolizin-2(6H)-one (851755-97-0)

Guidance literature:

Multi-step reaction with 10 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

With hydrogenchloride; carbon tetrabromide; hydrogen; oxygen; titanium tetrachloride; toluene-4-sulfonic acid; hydrazine hydrate; 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:

(S)-1-(3-Benzyloxy-4-methoxy-phenyl)-2-(2-methyl-[1,3]dioxolan-2-yl)-ethylamine (851755-92-5) → (4S,9aS)-4-(3-(tert-butyldimethylsilyloxy)-4-methoxyphenyl)hexahydro-1H-quinolizin-2(6H)-one (851755-97-0)

Guidance literature:

Multi-step reaction with 6 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

With hydrogenchloride; carbon tetrabromide; hydrogen; titanium tetrachloride; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; chloroform; triethylamine; 2: Mannich-type cyclization;

DOI:10.1016/j.tetlet.2005.02.110

upstream raw materials:

(4S,9aS)-4-(3-hydroxy-4-methoxyphenyl)hexahydro-1H-quinolizin-2(6H)-one

t-butyldimethylsiyl triflate

(S)-1-(3-Benzyloxy-4-methoxy-phenyl)-but-3-enylamine

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

Downstream raw materials:

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

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