(S)-6-(4-Benzyloxy-phenyl)-7-methyl-1,2,3,5,8,8a-hexahydro-indolizine

Base Information

• Chemical Name: (S)-6-(4-Benzyloxy-phenyl)-7-methyl-1,2,3,5,8,8a-hexahydro-indolizine
• CAS No.: 549548-39-2
• Molecular Formula: C₂₂H₂₅NO
• Molecular Weight: 319.447
• Mol file: 549548-39-2.mol

Synonyms:(S)-6-(4-Benzyloxy-phenyl)-7-methyl-1,2,3,5,8,8a-hexahydro-indolizine

Chemical Property of (S)-6-(4-Benzyloxy-phenyl)-7-methyl-1,2,3,5,8,8a-hexahydro-indolizine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-6-(4-Benzyloxy-phenyl)-7-methyl-1,2,3,5,8,8a-hexahydro-indolizine

There total 10 articles about (S)-6-(4-Benzyloxy-phenyl)-7-methyl-1,2,3,5,8,8a-hexahydro-indolizine 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: 86.0%

6-(4-benzyloxy-phenyl)-7-methyl-1,5,8,8a-tetrahydro-2H-indolizin-3-one (549548-37-0) → (S)-6-(4-Benzyloxy-phenyl)-7-methyl-1,2,3,5,8,8a-hexahydro-indolizine (549548-39-2)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/S0040-4039(03)00563-X

Reference yield:

(S)-Pyroglutaminol (17342-08-4) → (S)-6-(4-Benzyloxy-phenyl)-7-methyl-1,2,3,5,8,8a-hexahydro-indolizine (549548-39-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 88 percent / Et₃N; DMAP / CH₂Cl₂ / 20 °C

2.1: 93 percent / tetrahydrofuran; diethyl ether / -78 - 0 °C

3.1: 90 percent / NaH / tetrahydrofuran; hexamethylphosphoric acid triamide / 20 °C

4.1: O₃ / methanol / -78 °C

4.2: 99 percent / Me₂S / methanol / -78 - 20 °C

5.1: 30 percent / TiCl₃(THF)3; Zn-Cu / 1,2-dimethoxy-ethane / 48 h / 80 °C

6.1: 86 percent / LiAlH₄ / tetrahydrofuran / 20 °C

With dmap; lithium aluminium tetrahydride; titanium trichloride tris(tetrahydrofuran); copper; sodium hydride; ozone; triethylamine; zinc; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; diethyl ether; dichloromethane; 5.1: McMurry coupling;

DOI:10.1016/S0040-4039(03)00563-X

Reference yield:

(4-benzyloxy-phenyl)-acetic acid methyl ester (68641-16-7) → (S)-6-(4-Benzyloxy-phenyl)-7-methyl-1,2,3,5,8,8a-hexahydro-indolizine (549548-39-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 54 percent / Cs₂CO₃; tris[2-(2-methoxyethoxy)ethyl]amine / toluene / 85 °C

2.1: DIBAL / CH₂Cl₂ / -78 °C

3.1: CBr₄; PPh₃ / CH₂Cl₂ / 20 °C

4.1: 90 percent / NaH / tetrahydrofuran; hexamethylphosphoric acid triamide / 20 °C

5.1: O₃ / methanol / -78 °C

5.2: 99 percent / Me₂S / methanol / -78 - 20 °C

6.1: 30 percent / TiCl₃(THF)3; Zn-Cu / 1,2-dimethoxy-ethane / 48 h / 80 °C

7.1: 86 percent / LiAlH₄ / tetrahydrofuran / 20 °C

With lithium aluminium tetrahydride; titanium trichloride tris(tetrahydrofuran); carbon tetrabromide; Tris(3,6-dioxaheptyl)amine; copper; sodium hydride; diisobutylaluminium hydride; caesium carbonate; ozone; triphenylphosphine; zinc; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; dichloromethane; toluene; 6.1: McMurry coupling;

DOI:10.1016/S0040-4039(03)00563-X

upstream raw materials:

6-(4-benzyloxy-phenyl)-7-methyl-1,5,8,8a-tetrahydro-2H-indolizin-3-one

(4-benzyloxy-phenyl)-acetic acid methyl ester

(S)-toluene-4-sulfonic acid 5-oxo-pyrrolidin-2-ylmethyl ester

methyl 2-(4'-benzyloxyphenyl)propenoate

Downstream raw materials:

4-[(8aS)-7-methyl-1,2,3,5,8,8a-hexahydroindolizin-6-yl]phenol