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

Base Information

• Chemical Name: (1S,6S)-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonan-2-one
• CAS No.: 895138-20-2
• Molecular Formula: C₁₆H₂₁NO
• Molecular Weight: 243.349
• Mol file: 895138-20-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about (1S,6S)-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonan-2-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: 97.0%

(1S,2S,6S)-(+)-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonan-2-ol (895138-16-6) → (1S,6S)-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonan-2-one (895138-20-2)

Guidance literature:

(1S,2S,6S)-(+)-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonan-2-ol; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 0.5h; Inert atmosphere;

With triethylamine; In dichloromethane; at -78 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tet.2018.04.057

Reference yield:

(R)-1-phenyl-ethyl-amine (3886-69-9) → (1S,6S)-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonan-2-one (895138-20-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 33 percent / methanol / 72 h / 120 °C

2.1: tetrahydrofuran / 5 h / 0 °C

2.2: 61 percent / NaBH₄; aq. NaOH / tetrahydrofuran / 0.5 h / 0 - 20 °C

3.1: 85 percent / oxalyl chloride; triethylamine; DMSO / CH₂Cl₂ / -78 - 25 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 3.1: Moffat-Swern oxidation;

DOI:10.1021/jm060122n

Reference yield:

(Z)-9-oxabicyclo[6.1.0]non-4-ene (19740-90-0,57378-34-4,65207-47-8,73176-71-3,73176-86-0,117468-08-3,637-90-1) → (1S,6S)-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonan-2-one (895138-20-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: methanol / 16 h / Microwave irradiation; Heating; Sealed tube

2.1: mercury(II) diacetate / water; tetrahydrofuran / 0.5 h / 0 °C

2.2: 0.5 h / 0 - 20 °C

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

3.2: 1 h / -78 °C / Inert atmosphere

With oxalyl dichloride; mercury(II) diacetate; dimethyl sulfoxide; In tetrahydrofuran; methanol; dichloromethane; water; 3.1: |Swern Oxidation / 3.2: |Swern Oxidation;

DOI:10.1016/j.tet.2018.04.057

upstream raw materials:

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

(R)-1-phenyl-ethyl-amine

(Z)-9-oxabicyclo[6.1.0]non-4-ene

Downstream raw materials:

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

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

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

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