1-[(S)-2-((S)-12-Azido-tridecyl)-pyrrolidin-1-yl]-2-benzyloxy-ethanone

Base Information

• Chemical Name: 1-[(S)-2-((S)-12-Azido-tridecyl)-pyrrolidin-1-yl]-2-benzyloxy-ethanone
• CAS No.: 196600-30-3
• Molecular Formula: C₂₆H₄₂N₄O₂
• Molecular Weight: 442.645
• Mol file: 196600-30-3.mol

Synonyms:1-[(S)-2-((S)-12-Azido-tridecyl)-pyrrolidin-1-yl]-2-benzyloxy-ethanone

Chemical Property of 1-[(S)-2-((S)-12-Azido-tridecyl)-pyrrolidin-1-yl]-2-benzyloxy-ethanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(S)-2-((S)-12-Azido-tridecyl)-pyrrolidin-1-yl]-2-benzyloxy-ethanone

There total 11 articles about 1-[(S)-2-((S)-12-Azido-tridecyl)-pyrrolidin-1-yl]-2-benzyloxy-ethanone 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: 90.0%

Benzyloxyacetyl chloride (19810-31-2) + (S)-2-((S)-12-Azido-tridecyl)-pyrrolidine (196600-28-9) → 1-[(S)-2-((S)-12-Azido-tridecyl)-pyrrolidin-1-yl]-2-benzyloxy-ethanone (196600-30-3)

Guidance literature:

With TEA; In dichloromethane; at 0 ℃; for 12h;

DOI:10.1016/S0040-4039(97)01491-3

Reference yield:

D-prolinol (68832-13-3) → 1-[(S)-2-((S)-12-Azido-tridecyl)-pyrrolidin-1-yl]-2-benzyloxy-ethanone (196600-30-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 98 percent / CH₂Cl₂ / 0 deg C, 0.5 h then 25 deg C, 12 h

2: 88 percent / Py*SO₃, TEA / dimethylsulfoxide / 0.25 h / -10 - 15 °C

3: 84 percent / NaN(TMS)2 / tetrahydrofuran; toluene; hexamethylphosphoric acid triamide / 1 h / -78 - 25 °C

4: 1.) Pd(Ph)4, CuI, n-BuNH₂; 2.) hydrogen / 2.) Pd/C / 1.) C₆H₆, 25 deg C, 12 h; THF, 48 h

5: 89 percent / DEAD, Ph₃P / CH₂Cl₂ / 0.5 h / -50 °C

6: 95 percent / KOH / methanol / 12 h / 25 °C

7: 90 percent / DEAD, Ph₃P, (Ph)2PON₃ / tetrahydrofuran / 24 h / 25 °C

8: 63 percent / 1.) HCl; 2.) KOH/H₂O / ethyl acetate / 0.5 h / 25 °C

9: 90 percent / TEA / CH₂Cl₂ / 12 h / 0 °C

With hydrogenchloride; potassium hydroxide; copper(l) iodide; Pd(Ph)4; TEA; diphenylphosphoranyl azide; water; hydrogen; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; N-butylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; dimethyl sulfoxide; ethyl acetate; toluene;

DOI:10.1016/S0040-4039(97)01491-3

Reference yield:

1,7-Octadiyne (871-84-1) → 1-[(S)-2-((S)-12-Azido-tridecyl)-pyrrolidin-1-yl]-2-benzyloxy-ethanone (196600-30-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 71 percent / n-BuLi, Li₂CuCl₄ / tetrahydrofuran; hexamethylphosphoric acid triamide / 12 h / -20 °C

2: 1.) Pd(Ph)4, CuI, n-BuNH₂; 2.) hydrogen / 2.) Pd/C / 1.) C₆H₆, 25 deg C, 12 h; THF, 48 h

3: 89 percent / DEAD, Ph₃P / CH₂Cl₂ / 0.5 h / -50 °C

4: 95 percent / KOH / methanol / 12 h / 25 °C

5: 90 percent / DEAD, Ph₃P, (Ph)2PON₃ / tetrahydrofuran / 24 h / 25 °C

6: 63 percent / 1.) HCl; 2.) KOH/H₂O / ethyl acetate / 0.5 h / 25 °C

7: 90 percent / TEA / CH₂Cl₂ / 12 h / 0 °C

With hydrogenchloride; potassium hydroxide; copper(l) iodide; n-butyllithium; dilithium tetrachlorocuprate; Pd(Ph)4; TEA; diphenylphosphoranyl azide; water; hydrogen; N-butylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; ethyl acetate;

DOI:10.1016/S0040-4039(97)01491-3

upstream raw materials:

Benzyloxyacetyl chloride

(S)-2-((S)-12-Azido-tridecyl)-pyrrolidine

D-prolinol

1,7-Octadiyne