Phosphoric acid, 1-(1-methyl-1-nitroethyl)-4-(2-propenylamino)butyl diphenyl ester

Base Information

• Chemical Name: Phosphoric acid, 1-(1-methyl-1-nitroethyl)-4-(2-propenylamino)butyl diphenyl ester
• CAS No.: 350036-89-4
• Molecular Formula: C22H29N2O6P
• Molecular Weight: 448.456
• Mol file: 350036-89-4.mol

Synonyms:

Chemical Property of Phosphoric acid, 1-(1-methyl-1-nitroethyl)-4-(2-propenylamino)butyl diphenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Phosphoric acid, 1-(1-methyl-1-nitroethyl)-4-(2-propenylamino)butyl diphenyl ester

There total 5 articles about Phosphoric acid, 1-(1-methyl-1-nitroethyl)-4-(2-propenylamino)butyl diphenyl ester 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: 80.0%

3-(diphenyl-phosphoryloxy)-6-[N-allyl-N-(tert-butyloxycarbonyl)]amino-2-methyl-2-nitro-hexane (350036-88-3) → 3-(diphenyl-phosphoryloxy)-6-allylamino-2-methyl-2-nitro-hexane (350036-89-4)

Guidance literature:

With 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1021/ol015965h DOI:10.1021/ja035639s

Reference yield:

N-allyl 4-hydroxybutyramide (98435-58-6) → 3-(diphenyl-phosphoryloxy)-6-allylamino-2-methyl-2-nitro-hexane (350036-89-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 75 percent / LiAlH₄ / tetrahydrofuran / 18 h / Heating

2: 70 percent / triethylamine / tetrahydrofuran / 12 h / 20 °C

3: 87 percent / PCC; MS 4 Angstroem / CH₂Cl₂ / 2 h

4: potassium tert-butoxide / 2-methyl-propan-2-ol; acetonitrile / 24 h / 0 - 20 °C

5: 0.61 g / DMAP / CH₂Cl₂ / 0 - 20 °C

6: 80 percent / TMSOTf; 2,6-lutidine / CH₂Cl₂ / 0.5 h / 20 °C

With 2,6-dimethylpyridine; dmap; lithium aluminium tetrahydride; trimethylsilyl trifluoromethanesulfonate; MS 4 Angstroem; potassium tert-butylate; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; acetonitrile; tert-butyl alcohol;

DOI:10.1021/ja035639s

Reference yield:

4-[N-allyl N-(tert-butyloxycarbonyl)]amino-1-butanol (176686-16-1) → 3-(diphenyl-phosphoryloxy)-6-allylamino-2-methyl-2-nitro-hexane (350036-89-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / PCC; MS 4 Angstroem / CH₂Cl₂ / 2 h

2: potassium tert-butoxide / 2-methyl-propan-2-ol; acetonitrile / 24 h / 0 - 20 °C

3: 0.61 g / DMAP / CH₂Cl₂ / 0 - 20 °C

4: 80 percent / TMSOTf; 2,6-lutidine / CH₂Cl₂ / 0.5 h / 20 °C

With 2,6-dimethylpyridine; dmap; trimethylsilyl trifluoromethanesulfonate; MS 4 Angstroem; potassium tert-butylate; pyridinium chlorochromate; In dichloromethane; acetonitrile; tert-butyl alcohol;

DOI:10.1021/ja035639s

upstream raw materials:

3-(diphenyl-phosphoryloxy)-6-[N-allyl-N-(tert-butyloxycarbonyl)]amino-2-methyl-2-nitro-hexane

N-allyl 4-hydroxybutyramide

4-[N-allyl N-(tert-butyloxycarbonyl)]amino-1-butanol

4-[N-allyl N-(tert-butyloxycarbonyl)]aminobutanal

Refernces

• 1、 Crich, David,Ranganathan, Krishnakumar,Huang, Xianhai. "Generation and reaction of alkene radical cations under nonoxidizing conditions: Synthesis of the pyrrolizidine nucleus". . p. 1917 - 1919. Retrieved 2007/10/03.