(1R,4S)-1,7,7-trimethyl-2-[2-(triphenylphosphanylidene)-acetyl]-2-aza-bicyclo[2.2.1]heptan-3-one

Base Information

• Chemical Name: (1R,4S)-1,7,7-trimethyl-2-[2-(triphenylphosphanylidene)-acetyl]-2-aza-bicyclo[2.2.1]heptan-3-one
• CAS No.: 911708-82-2
• Molecular Formula: C₂₉H₃₀NO₂P
• Molecular Weight: 455.536
• Mol file: 911708-82-2.mol

Synonyms:(1R,4S)-1,7,7-trimethyl-2-[2-(triphenylphosphanylidene)-acetyl]-2-aza-bicyclo[2.2.1]heptan-3-one

Chemical Property of (1R,4S)-1,7,7-trimethyl-2-[2-(triphenylphosphanylidene)-acetyl]-2-aza-bicyclo[2.2.1]heptan-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4S)-1,7,7-trimethyl-2-[2-(triphenylphosphanylidene)-acetyl]-2-aza-bicyclo[2.2.1]heptan-3-one

There total 2 articles about (1R,4S)-1,7,7-trimethyl-2-[2-(triphenylphosphanylidene)-acetyl]-2-aza-bicyclo[2.2.1]heptan-3-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: 90.0%

Bestmann ylide (73818-55-0,15596-07-3) + (1R)-1,7,7-trimethyl-2-azabicyclo<2.2.1>heptan-3-one (24326-89-4) → (1R,4S)-1,7,7-trimethyl-2-[2-(triphenylphosphanylidene)-acetyl]-2-aza-bicyclo[2.2.1]heptan-3-one (911708-82-2)

Guidance literature:

In toluene; for 24h; Heating;

DOI:10.1021/jo061732y DOI:10.1021/ja063532+

Reference yield:

methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) → (1R,4S)-1,7,7-trimethyl-2-[2-(triphenylphosphanylidene)-acetyl]-2-aza-bicyclo[2.2.1]heptan-3-one (911708-82-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / NaNH₂; bis(trimethylsilyl)amine / toluene / 24 h / 60 °C

2: 90 percent / toluene / 24 h / Heating

With sodium amide; 1,1,1,3,3,3-hexamethyl-disilazane; In toluene;

DOI:10.1021/ja063532+

Reference yield: 98.0%

(1R,4S)-1,7,7-trimethyl-2-[2-(triphenylphosphanylidene)-acetyl]-2-aza-bicyclo[2.2.1]heptan-3-one (911708-82-2) + 1-Iodohexane (638-45-9) → (1R,4S)-1,7,7-trimethyl-2-[2-(triphenylphospanylidene)octanoyl]-2-azabicyclo[2.2.1]heptan-3-one

Guidance literature:

(1R,4S)-1,7,7-trimethyl-2-[2-(triphenylphosphanylidene)-acetyl]-2-aza-bicyclo[2.2.1]heptan-3-one; 1-Iodohexane; In acetonitrile; for 2h; Heating;

With sodium hydroxide; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/jo061732y

upstream raw materials:

Bestmann ylide

(1R)-1,7,7-trimethyl-2-azabicyclo<2.2.1>heptan-3-one

methyl (triphenylphosphoranylidene)acetate

Downstream raw materials:

(1R,4S)-1,7,7-trimethyl-2-[2-(triphenylphospanylidene)propionyl]-2-azabicyclo[2.2.1]heptan-3-one