N-benzyl-N-(tert-butyloxycarbonyl)-5-hydroxy-6-methyl-6-nitroheptylamine

Base Information

• Chemical Name: N-benzyl-N-(tert-butyloxycarbonyl)-5-hydroxy-6-methyl-6-nitroheptylamine
• CAS No.: 615268-16-1
• Molecular Formula: C₂₀H₃₂N₂O₅
• Molecular Weight: 380.484
• Mol file: 615268-16-1.mol

Synonyms:N-benzyl-N-(tert-butyloxycarbonyl)-5-hydroxy-6-methyl-6-nitroheptylamine

Chemical Property of N-benzyl-N-(tert-butyloxycarbonyl)-5-hydroxy-6-methyl-6-nitroheptylamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-benzyl-N-(tert-butyloxycarbonyl)-5-hydroxy-6-methyl-6-nitroheptylamine

There total 1 articles about N-benzyl-N-(tert-butyloxycarbonyl)-5-hydroxy-6-methyl-6-nitroheptylamine 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%

2-nitropropane (79-46-9) + benzyl-(5-oxo-pentyl)-carbamic acid tert-butyl acid (213772-26-0) → N-benzyl-N-(tert-butyloxycarbonyl)-5-hydroxy-6-methyl-6-nitroheptylamine (615268-16-1)

Guidance literature:

With potassium tert-butylate; In acetonitrile; at 25 ℃;

DOI:10.1021/ol035564x

Reference yield: 93.0%

N-benzyl-N-(tert-butyloxycarbonyl)-5-hydroxy-6-methyl-6-nitroheptylamine (615268-16-1) → N-benzyl-N-(tert-butyloxycarbonyl)-6-methyl-6-nitro-5-oxo-heptylamine (615268-17-2)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃;

DOI:10.1021/ol035564x

Reference yield:

N-benzyl-N-(tert-butyloxycarbonyl)-5-hydroxy-6-methyl-6-nitroheptylamine (615268-16-1) → (5R)-N-benzyl-5-diphenylphosphatoxy-6-methyl-6-nitroheptylamine (615268-23-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 1.33 h / cooling

2: (S)-(-)-α,α-diphenyl-2-pyrrolidinemethanol; borane dimethyl sulfide complex / tetrahydrofuran / 0.83 h / Heating

3: DMAP / CH₂Cl₂ / 20 °C

4: trifluoroacetic acid / CH₂Cl₂ / 20 °C

With dmap; oxalyl dichloride; (S)-diphenylprolinol; dimethylsulfide borane complex; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; 1: Swern oxidation;

DOI:10.1016/j.tet.2006.03.063

upstream raw materials:

2-nitropropane

benzyl-(5-oxo-pentyl)-carbamic acid tert-butyl acid

Downstream raw materials:

N-benzyl-N-(tert-butyloxycarbonyl)-6-methyl-6-nitro-5-oxo-heptylamine

(5R)-N-benzyl-N-(tert-butyloxycarbonyl)-5-hydroxy-6-methyl-6-nitroheptylamine

(5R)-N-benzyl-5-diphenylphosphatoxy-6-methyl-6-nitroheptylamine

(5R)-N-benzyl-N-(tert-butyloxycarbonyl)-5-diphenylphosphatoxy-6-methyl-6-nitroheptylamine