8-cyclopropylmethyl-6α-hydroxy-6β-phenyl-8-azabicyclo<3.2.1>octane

Base Information

• Chemical Name: 8-cyclopropylmethyl-6α-hydroxy-6β-phenyl-8-azabicyclo<3.2.1>octane
• CAS No.: 100986-58-1
• Molecular Formula: C₁₇H₂₃NO
• Molecular Weight: 257.376
• Mol file: 100986-58-1.mol

Synonyms:

Chemical Property of 8-cyclopropylmethyl-6α-hydroxy-6β-phenyl-8-azabicyclo<3.2.1>octane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-cyclopropylmethyl-6α-hydroxy-6β-phenyl-8-azabicyclo<3.2.1>octane

There total 8 articles about 8-cyclopropylmethyl-6α-hydroxy-6β-phenyl-8-azabicyclo<3.2.1>octane 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:

6α-hydroxy-6β-phenyl-8-(2-phenylethyl)-8-azabicyclo<3.2.1>octane (100986-57-0) → 8-cyclopropylmethyl-6α-hydroxy-6β-phenyl-8-azabicyclo<3.2.1>octane (100986-58-1)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 24h; Heating;

Reference yield:

acetonedicarboxylic acid (542-05-2) → 8-cyclopropylmethyl-6α-hydroxy-6β-phenyl-8-azabicyclo<3.2.1>octane (100986-58-1)

Guidance literature:

Multi-step reaction with 8 steps

1: sodium acetate, HCl, K₂CO₃ / H₂O / 48 h / Ambient temperature; pH=4-5

2: hydrazine hydrate / ethanol / 3 h / 120 °C

3: KOH / 130 degC, 1 h; 160 degC, 2 h; 190 degC, 1.5 h

4: 48 percent / chromium trioxide / acetic acid / 70-80 degC, 16 h; 100 degC, 2 h

5: tetrahydrofuran / 6 h / Heating

6: 1.) trichloroethyl chloroformate, K₂CO₃; 2.) acetic acid, zinc / 1.) toluene, 2 d, reflux; 2.) water, 16 h, room temperature

7: triethylamine / diethyl ether; tetrahydrofuran / 144 h / Heating

8: LiAlH₄ / diethyl ether / 24 h / Heating

With chromium(VI) oxide; hydrogenchloride; potassium hydroxide; lithium aluminium tetrahydride; trichloroethyl chloroformate; sodium acetate; potassium carbonate; hydrazine hydrate; acetic acid; triethylamine; zinc; In tetrahydrofuran; diethyl ether; ethanol; water; acetic acid;

Reference yield:

8-methyl-8-azabicyclo<3.2.1>octane (18700-22-6) → 8-cyclopropylmethyl-6α-hydroxy-6β-phenyl-8-azabicyclo<3.2.1>octane (100986-58-1)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrahydrofuran / 6 h / Heating

2: 1.) trichloroethyl chloroformate, K₂CO₃; 2.) acetic acid, zinc / 1.) toluene, 2 d, reflux; 2.) water, 16 h, room temperature

3: triethylamine / diethyl ether; tetrahydrofuran / 144 h / Heating

4: LiAlH₄ / diethyl ether / 24 h / Heating

With lithium aluminium tetrahydride; trichloroethyl chloroformate; potassium carbonate; acetic acid; triethylamine; zinc; In tetrahydrofuran; diethyl ether;

upstream raw materials:

6α-hydroxy-6β-phenyl-8-(2-phenylethyl)-8-azabicyclo<3.2.1>octane

acetonedicarboxylic acid

6β-hydroxy-8-methyl-8-azabicyclo<3.2.1>octane

8-methyl-8-azabicyclo<3.2.1>octane

Downstream raw materials:

Acetic acid (1S,5R,6S,8S)-8-cyclopropylmethyl-6-phenyl-8-aza-bicyclo[3.2.1]oct-6-yl ester

Refernces