2-Azabicyclo[2.2.1]heptane,3-(1-pyrrolidinylmethyl)-,(1S,3R,4R)-(9CI)

Base Information

• Chemical Name: 2-Azabicyclo[2.2.1]heptane,3-(1-pyrrolidinylmethyl)-,(1S,3R,4R)-(9CI)
• CAS No.: 215674-20-7
• Molecular Formula: C₁₁H₂₀N₂
• Molecular Weight: 180.293
• Mol file: 215674-20-7.mol

Synonyms:(-)-(1S,3R,4R)-3-(1-pyrrolidinylmethyl)-2-azabicyclo[2.2.1]heptane

Chemical Property of 2-Azabicyclo[2.2.1]heptane,3-(1-pyrrolidinylmethyl)-,(1S,3R,4R)-(9CI)

Chemical Property:

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Azabicyclo[2.2.1]heptane,3-(1-pyrrolidinylmethyl)-,(1S,3R,4R)-(9CI)

There total 14 articles about 2-Azabicyclo[2.2.1]heptane,3-(1-pyrrolidinylmethyl)-,(1S,3R,4R)-(9CI) 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: 92.0%

(1R,3R,4S)-2-Aza-bicyclo[2.2.1]hept-5-en-3-yl-pyrrolidin-1-yl-methanone (307530-60-5) → (1S,3R,4R)-3-pyrrolidin-1-ylmethyl-2-azabicyclo[2.2.1]heptane (215674-22-9,215674-20-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; Heating;

DOI:10.1021/jo005508z

Reference yield: 89.0%

(1S,3R,4R)-3-(N-pyrrolidinyl)methyl-2-[(S)-1-phenylethyl]-2-azabicyclo[2.2.1]heptane (215674-18-3) → (1S,3R,4R)-3-pyrrolidin-1-ylmethyl-2-azabicyclo[2.2.1]heptane (215674-22-9,215674-20-7)

Guidance literature:

With hydrogen; acetic acid; palladium dihydroxide; In methanol; under 760 Torr;

DOI:10.1021/ja982381a

Reference yield:

(1S,3R,4R)-2-[(S)-1-Phenylethylamino]-2-azabicyclo[2.2.1]heptane-3-carboxaldehyde (215674-17-2) → (1S,3R,4R)-3-pyrrolidin-1-ylmethyl-2-azabicyclo[2.2.1]heptane (215674-22-9,215674-20-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 3A molecular sieves / methanol / 0.25 h

1.2: 91 percent / NaBH₃CN / methanol / 12 h / 20 °C

2.1: 89 percent / H₂; AcOH / 20percent Pd(OH)2/C / methanol / 24 h / 20 °C / 760.05 Torr

With 3 A molecular sieve; hydrogen; acetic acid; 20percent Pd(OH)2/C; In methanol; 1.1: Condensation / 1.2: Reduction / 2.1: Hydrogenolysis;

DOI:10.1021/ja000545t

upstream raw materials:

(1S,3R,4R)-3-(N-pyrrolidinyl)methyl-2-[(S)-1-phenylethyl]-2-azabicyclo[2.2.1]heptane

(1R,3R,4S)-2-Aza-bicyclo[2.2.1]hept-5-en-3-yl-pyrrolidin-1-yl-methanone

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

(1S,3R,4R)-2-[(S)-1-Phenylethylamino]-2-azabicyclo[2.2.1]heptane-3-carboxaldehyde

Refernces

• 1、 Modin, Stefan A.,Andersson, Pher G.. "Rapid access to enantiopure bicyclic diamines via aza-Diels-Alder reaction of iminoamides". . p. 6736 - 6738. Retrieved 2007/10/03.