(1R,6R)-3-allyl-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonane-2-carbonitrile

Base Information

• Chemical Name: (1R,6R)-3-allyl-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonane-2-carbonitrile
• CAS No.: 895138-31-5
• Molecular Formula: C₂₀H₂₆N₂
• Molecular Weight: 294.44
• Mol file: 895138-31-5.mol

Synonyms:(1R,6R)-3-allyl-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonane-2-carbonitrile

Chemical Property of (1R,6R)-3-allyl-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonane-2-carbonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,6R)-3-allyl-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonane-2-carbonitrile

There total 5 articles about (1R,6R)-3-allyl-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonane-2-carbonitrile 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: 79.0%

(1R,6R)-3-allyl-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonan-2-one (895138-30-4) + [(p-methylphenyl)sulfonylmethyl]isonitrile (38622-91-2,36635-61-7) → (1R,6R)-3-allyl-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonane-2-carbonitrile (895138-31-5)

Guidance literature:

With potassium tert-butylate; In methanol; 1,2-dimethoxyethane; at 50 ℃;

DOI:10.1021/jm060122n

Reference yield:

(1R,8R)-(-)-trans-8-[(R)-1-phenylethylamino]cyclooct-4-enol → (1R,6R)-3-allyl-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonane-2-carbonitrile (895138-31-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetrahydrofuran / 5 h / 0 °C

1.2: 60 percent / NaBH₄; aq. NaOH / tetrahydrofuran / 0.5 h / 0 - 20 °C

2.1: 85 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 25 °C

3.1: KN[Si(CH₃)3]2 / tetrahydrofuran / -78 °C

3.2: Et₃B / tetrahydrofuran / -78 °C

3.3: 82 percent / tetrahydrofuran / -78 - 20 °C

4.1: 79 percent / t-BuOK / 1,2-dimethoxy-ethane; methanol / 50 °C

With oxalyl dichloride; potassium tert-butylate; potassium hexamethylsilazane; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; 2.1: Moffat-Swern oxidation;

DOI:10.1021/jm060122n

Reference yield:

(1R,6R)-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonan-2-one (895138-29-1) → (1R,6R)-3-allyl-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonane-2-carbonitrile (895138-31-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: KN[Si(CH₃)3]2 / tetrahydrofuran / -78 °C

1.2: Et₃B / tetrahydrofuran / -78 °C

1.3: 82 percent / tetrahydrofuran / -78 - 20 °C

2.1: 79 percent / t-BuOK / 1,2-dimethoxy-ethane; methanol / 50 °C

With potassium tert-butylate; potassium hexamethylsilazane; In tetrahydrofuran; methanol; 1,2-dimethoxyethane;

DOI:10.1021/jm060122n

upstream raw materials:

(1R,6R)-3-allyl-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonan-2-one

[(p-methylphenyl)sulfonylmethyl]isonitrile

(1R,6R)-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonan-2-one

(1R,2R,6R)-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonan-2-ol

Downstream raw materials:

(1R,6R)-9-[(R)-1-phenylethyl]-pyrido[3,4-b]homotropane

(1R,6R)-3-allyl-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonane-2-carbaldehyde