(+)-(S)-2-amino-3-phenyl-1-((1R,5S)-1,6,6-trimethyl-8-azabicyclo[3.2.1]octan-8-yl)propan-1-one

Base Information

• Chemical Name: (+)-(S)-2-amino-3-phenyl-1-((1R,5S)-1,6,6-trimethyl-8-azabicyclo[3.2.1]octan-8-yl)propan-1-one
• CAS No.: 1421636-94-3
• Molecular Formula: C₁₉H₂₈N₂O
• Molecular Weight: 300.444
• Mol file: 1421636-94-3.mol

Synonyms:

Chemical Property of (+)-(S)-2-amino-3-phenyl-1-((1R,5S)-1,6,6-trimethyl-8-azabicyclo[3.2.1]octan-8-yl)propan-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(S)-2-amino-3-phenyl-1-((1R,5S)-1,6,6-trimethyl-8-azabicyclo[3.2.1]octan-8-yl)propan-1-one

There total 6 articles about (+)-(S)-2-amino-3-phenyl-1-((1R,5S)-1,6,6-trimethyl-8-azabicyclo[3.2.1]octan-8-yl)propan-1-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:

tert-butyl ((S)-1-oxo-3-phenyl-1-(1,6,6-trimethyl-8-azabicyclo[3.2.1]octan-8-yl)propan-2-yl)carbamate → (+)-(S)-2-amino-3-phenyl-1-((1R,5S)-1,6,6-trimethyl-8-azabicyclo[3.2.1]octan-8-yl)propan-1-one (1421636-94-3) + (+)-(S)-2-amino-3-phenyl-1-((1S,5R)-1,6,6-trimethyl-8-azabicyclo[3.2.1]octan-8-yl)propan-1-one (1421636-84-1)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jo3025972

Reference yield:

(±)-8-benzyl-1,6,6-trimethyl-8-azabicyclo[3.2.1]octane → (+)-(S)-2-amino-3-phenyl-1-((1R,5S)-1,6,6-trimethyl-8-azabicyclo[3.2.1]octan-8-yl)propan-1-one (1421636-94-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: palladium 10% on activated carbon; hydrogen / methanol / 17 h / 760.05 Torr / Inert atmosphere

1.2: Inert atmosphere

2.1: sodium hydroxide / diethyl ether; water

3.1: bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 72 h / 0 - 4 °C / Inert atmosphere

4.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere

With palladium 10% on activated carbon; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium hydroxide; In methanol; diethyl ether; dichloromethane; water;

DOI:10.1021/jo3025972

Reference yield:

(±)-8-benzyl-1,6,6-trimethyl-8-azabicyclo[3.2.1]octan-3-one → (+)-(S)-2-amino-3-phenyl-1-((1R,5S)-1,6,6-trimethyl-8-azabicyclo[3.2.1]octan-8-yl)propan-1-one (1421636-94-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: hydrazine hydrate; potassium hydroxide / diethylene glycol / 24 h / 190 °C / Inert atmosphere

2.1: palladium 10% on activated carbon; hydrogen / methanol / 17 h / 760.05 Torr / Inert atmosphere

2.2: Inert atmosphere

3.1: sodium hydroxide / diethyl ether; water

4.1: bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 72 h / 0 - 4 °C / Inert atmosphere

5.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere

With palladium 10% on activated carbon; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; hydrazine hydrate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; potassium hydroxide; sodium hydroxide; In methanol; diethyl ether; dichloromethane; water; diethylene glycol; 1.1: |Wolff-Kishner Reduction;

DOI:10.1021/jo3025972

upstream raw materials:

2,2-dimethyl-4-oxopentenal