(4aR,5S)-1-(4-fluorophenyl)-4a-methyl-4,4a,5,6,7,8-hexahydro-1H-benzo[f]indazole-5-carbaldehyde

Base Information

• Chemical Name: (4aR,5S)-1-(4-fluorophenyl)-4a-methyl-4,4a,5,6,7,8-hexahydro-1H-benzo[f]indazole-5-carbaldehyde
• CAS No.: 614763-01-8
• Molecular Formula: C₁₉H₁₉FN₂O
• Molecular Weight: 310.371
• Mol file: 614763-01-8.mol

Synonyms:

Chemical Property of (4aR,5S)-1-(4-fluorophenyl)-4a-methyl-4,4a,5,6,7,8-hexahydro-1H-benzo[f]indazole-5-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aR,5S)-1-(4-fluorophenyl)-4a-methyl-4,4a,5,6,7,8-hexahydro-1H-benzo[f]indazole-5-carbaldehyde

There total 4 articles about (4aR,5S)-1-(4-fluorophenyl)-4a-methyl-4,4a,5,6,7,8-hexahydro-1H-benzo[f]indazole-5-carbaldehyde 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:

(8aS)-1,1-(1,2-ethylenedioxy)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-6-oxonaphthalene (61950-54-7) → (4aR,5S)-1-(4-fluorophenyl)-4a-methyl-4,4a,5,6,7,8-hexahydro-1H-benzo[f]indazole-5-carbaldehyde (614763-01-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: NaH; MeOH / benzene / 3 h / 20 °C

2.1: 2.26 g / sodium acetate; glacial acetic acid / 2 h / 20 °C

3.1: HCl / tetrahydrofuran / 3.5 h / 65 °C

4.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 0.25 h / 0 °C

4.2: tetrahydrofuran; toluene / 24 h / 20 °C

4.3: aq. HCl / tetrahydrofuran; methanol; toluene / 36 h / 20 °C

With hydrogenchloride; methanol; sodium acetate; potassium hexamethylsilazane; sodium hydride; acetic acid; In tetrahydrofuran; toluene; benzene;

DOI:10.1021/jm030585i

Reference yield:

(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione (33878-99-8) → (4aR,5S)-1-(4-fluorophenyl)-4a-methyl-4,4a,5,6,7,8-hexahydro-1H-benzo[f]indazole-5-carbaldehyde (614763-01-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 93 percent / p-toluenesulfonic acid; molecular sieves 4A / 0.38 h / 20 °C

2.1: NaH; MeOH / benzene / 3 h / 20 °C

3.1: 2.26 g / sodium acetate; glacial acetic acid / 2 h / 20 °C

4.1: HCl / tetrahydrofuran / 3.5 h / 65 °C

5.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 0.25 h / 0 °C

5.2: tetrahydrofuran; toluene / 24 h / 20 °C

5.3: aq. HCl / tetrahydrofuran; methanol; toluene / 36 h / 20 °C

With hydrogenchloride; methanol; 4 A molecular sieve; sodium acetate; potassium hexamethylsilazane; sodium hydride; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran; toluene; benzene;

DOI:10.1021/jm030585i

Reference yield:

(7'Z,8a'S)-7'-(hydroxymethylene)-8a'-methyl-3',4',8',8a'-tetrahydro-2'H-spiro[1,3-dioxolane-2,1'-naphthalen]-6'(7'H)-one → (4aR,5S)-1-(4-fluorophenyl)-4a-methyl-4,4a,5,6,7,8-hexahydro-1H-benzo[f]indazole-5-carbaldehyde (614763-01-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 2.26 g / sodium acetate; glacial acetic acid / 2 h / 20 °C

2.1: HCl / tetrahydrofuran / 3.5 h / 65 °C

3.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 0.25 h / 0 °C

3.2: tetrahydrofuran; toluene / 24 h / 20 °C

3.3: aq. HCl / tetrahydrofuran; methanol; toluene / 36 h / 20 °C

With hydrogenchloride; sodium acetate; potassium hexamethylsilazane; acetic acid; In tetrahydrofuran; toluene;

DOI:10.1021/jm030585i

upstream raw materials:

(8aS)-1,1-(1,2-ethylenedioxy)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-6-oxonaphthalene

(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

(4aS)-1-(4-fluorophenyl)-4a-methyl-1,4,4a,6,7,8-hexahydrospiro[benzo[f]indazole-5,2'-[1,3]dioxolane]

Downstream raw materials:

benzo[b]thiophen-3-yl-[1-(4-fluoro-phenyl)-4a-methyl-4,4a,5,6,7,8-hexahydro-1H-benzo[f]indazol-5-yl]-methanol

[1-(4-fluoro-phenyl)-4a-methyl-4,4a,5,6,7,8-hexahydro-1H-benzo[f]indazol-5-yl]-(6-fluoro-pyridin-3-yl)-methanol