1R,5S-(+)-5-(3-methoxyphenyl)-2-aza-bicyclo-[3.1.1]nonane

Base Information

• Chemical Name: 1R,5S-(+)-5-(3-methoxyphenyl)-2-aza-bicyclo-[3.1.1]nonane
• CAS No.: 51596-47-5
• Molecular Formula: C₁₅H₂₁NO
• Molecular Weight: 231.338
• Mol file: 51596-47-5.mol

Synonyms:1R,5S-(+)-5-(3-methoxyphenyl)-2-aza-bicyclo-[3.1.1]nonane

Chemical Property of 1R,5S-(+)-5-(3-methoxyphenyl)-2-aza-bicyclo-[3.1.1]nonane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1R,5S-(+)-5-(3-methoxyphenyl)-2-aza-bicyclo-[3.1.1]nonane

There total 4 articles about 1R,5S-(+)-5-(3-methoxyphenyl)-2-aza-bicyclo-[3.1.1]nonane 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: 93.0%

1R,5S-(-)-2-benzyl-5-(3-methoxyphenyl)-2-aza-bicyclo[3.3.1]nonane (938463-22-0) → 1R,5S-(+)-5-(3-methoxyphenyl)-2-aza-bicyclo-[3.1.1]nonane (51596-47-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 6h; under 3102.97 Torr;

DOI:10.1039/b618875c

Reference yield:

3-methoxyphenyl bromide (2398-37-0) → 1R,5S-(+)-5-(3-methoxyphenyl)-2-aza-bicyclo-[3.1.1]nonane (51596-47-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: n-BuLi / tetrahydrofuran / 2 h / -60 °C

1.2: tetrahydrofuran / 2 h / 20 °C

2.1: 51.4 g / p-toluenesulfonic acid monohydrate / toluene / 6 h / Heating

3.1: sec-BuLi / cyclohexane; tetrahydrofuran / 1 h / -40 °C

3.2: cyclohexane; tetrahydrofuran / 2 h / 0 °C

4.1: aq. H₃PO₄; formic acid / 72 h / 20 °C

5.1: 35.2 g / NaBH₄ / methanol / 2 h / 20 °C

6.1: (+)-di-O,O'-p-toluyl-D-tartaric acid / acetone / 0.33 h

6.2: NH₄OH

7.1: 93 percent / hydrogen / Pd/C / methanol / 6 h / 20 °C / 3102.97 Torr

With sodium tetrahydroborate; n-butyllithium; (2S,3S)-di-4-toluoyltartaric acid; hydrogen; sec.-butyllithium; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; formic acid; cyclohexane; phosphoric acid; acetone; toluene;

DOI:10.1039/b618875c

Reference yield:

C22H25NO (1026869-17-9) → 1R,5S-(+)-5-(3-methoxyphenyl)-2-aza-bicyclo-[3.1.1]nonane (51596-47-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: aq. H₃PO₄; formic acid / 72 h / 20 °C

2.1: 35.2 g / NaBH₄ / methanol / 2 h / 20 °C

3.1: (+)-di-O,O'-p-toluyl-D-tartaric acid / acetone / 0.33 h

3.2: NH₄OH

4.1: 93 percent / hydrogen / Pd/C / methanol / 6 h / 20 °C / 3102.97 Torr

With sodium tetrahydroborate; (2S,3S)-di-4-toluoyltartaric acid; hydrogen; palladium on activated charcoal; In methanol; formic acid; phosphoric acid; acetone;

DOI:10.1039/b618875c

upstream raw materials:

1R,5S-(-)-2-benzyl-5-(3-methoxyphenyl)-2-aza-bicyclo[3.3.1]nonane

C₂₂H₂₅NO

2-benzyl-5-(3-methoxyphenyl)-2-aza-bicyclo[3.3.1]nonane

3-methoxyphenyl bromide