(1S,3R,4R)-3-Bromomethyl-2-(toluene-4-sulfonyl)-2-aza-bicyclo[2.2.1]heptane

Base Information

• Chemical Name: (1S,3R,4R)-3-Bromomethyl-2-(toluene-4-sulfonyl)-2-aza-bicyclo[2.2.1]heptane
• CAS No.: 226958-99-2
• Molecular Formula: C₁₄H₁₈BrNO₂S
• Molecular Weight: 344.272
• Mol file: 226958-99-2.mol

Synonyms:(1S,3R,4R)-3-Bromomethyl-2-(toluene-4-sulfonyl)-2-aza-bicyclo[2.2.1]heptane

Chemical Property of (1S,3R,4R)-3-Bromomethyl-2-(toluene-4-sulfonyl)-2-aza-bicyclo[2.2.1]heptane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3R,4R)-3-Bromomethyl-2-(toluene-4-sulfonyl)-2-aza-bicyclo[2.2.1]heptane

There total 4 articles about (1S,3R,4R)-3-Bromomethyl-2-(toluene-4-sulfonyl)-2-aza-bicyclo[2.2.1]heptane 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: 60.0%

[(1S,3R,4R)-2-(Toluene-4-sulfonyl)-2-aza-bicyclo[2.2.1]hept-3-yl]-methanol (273721-40-7) → (1S,3R,4R)-3-Bromomethyl-2-(toluene-4-sulfonyl)-2-aza-bicyclo[2.2.1]heptane (226958-99-2)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1039/a901073d

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → (1S,3R,4R)-3-Bromomethyl-2-(toluene-4-sulfonyl)-2-aza-bicyclo[2.2.1]heptane (226958-99-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / Et₃N / CH₂Cl₂ / 20 °C

2: 95 percent / LiAlH₄ / tetrahydrofuran / 2 h / 20 °C

3: 60 percent / CBr₄ / PPh₃ / CH₂Cl₂ / 24 h / 20 °C

With lithium aluminium tetrahydride; carbon tetrabromide; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; 1: Tosylation / 2: Reduction / 3: Substitution;

DOI:10.1039/a901073d

Reference yield:

(1S,3R,4R)-2-aza-bicyclo<2.2.1>heptane-3-carboxylic acid ethyl ester (204327-17-3,245429-73-6,385808-62-8) → (1S,3R,4R)-3-Bromomethyl-2-(toluene-4-sulfonyl)-2-aza-bicyclo[2.2.1]heptane (226958-99-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / Et₃N / CH₂Cl₂ / 20 °C

2: 95 percent / LiAlH₄ / tetrahydrofuran / 2 h / 20 °C

3: 60 percent / CBr₄ / PPh₃ / CH₂Cl₂ / 24 h / 20 °C

With lithium aluminium tetrahydride; carbon tetrabromide; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; 1: Tosylation / 2: Reduction / 3: Substitution;

DOI:10.1039/a901073d

upstream raw materials:

[(1S,3R,4R)-2-(Toluene-4-sulfonyl)-2-aza-bicyclo[2.2.1]hept-3-yl]-methanol

p-toluenesulfonyl chloride

(1S,3R,4R)-2-aza-bicyclo<2.2.1>heptane-3-carboxylic acid ethyl ester

(1S,3R,4R)-2-(Toluene-4-sulfonyl)-2-aza-bicyclo[2.2.1]heptane-3-carboxylic acid ethyl ester