ethyl (2S,4S)-4-azido-1-benzylprolinate

Base Information

• Chemical Name: ethyl (2S,4S)-4-azido-1-benzylprolinate
• CAS No.: 627100-81-6
• Molecular Formula: C₁₄H₁₈N₄O₂
• Molecular Weight: 274.323
• Mol file: 627100-81-6.mol

Synonyms:ethyl (2S,4S)-4-azido-1-benzylprolinate

Chemical Property of ethyl (2S,4S)-4-azido-1-benzylprolinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (2S,4S)-4-azido-1-benzylprolinate

There total 5 articles about ethyl (2S,4S)-4-azido-1-benzylprolinate 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%

ethyl (2S,4R)-1-benzyl-4-(4-methylphenylsulfonyloxy)prolinate (627100-71-4) → ethyl (2S,4S)-4-azido-1-benzylprolinate (627100-81-6)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 60 ℃; for 7h;

DOI:10.1016/j.tetasy.2003.08.019

Reference yield:

trans-4-hydroxy-L-proline ethyl ester hydrochloride (33996-30-4) → ethyl (2S,4S)-4-azido-1-benzylprolinate (627100-81-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Et₃N / CHCl₃ / 6 h / Heating

1.2: 12.40 g / aq. NaOH / CHCl₃ / 20 °C

2.1: 57 percent / pyridine / 48 h / 20 °C

3.1: 92 percent / NaN₃ / dimethylformamide / 7 h / 60 °C

With pyridine; sodium azide; triethylamine; In chloroform; N,N-dimethyl-formamide;

DOI:10.1016/j.tetasy.2003.08.019

Reference yield:

benzyl bromide (100-39-0) → ethyl (2S,4S)-4-azido-1-benzylprolinate (627100-81-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Et₃N / CHCl₃ / 6 h / Heating

1.2: 12.40 g / aq. NaOH / CHCl₃ / 20 °C

2.1: 57 percent / pyridine / 48 h / 20 °C

3.1: 92 percent / NaN₃ / dimethylformamide / 7 h / 60 °C

With pyridine; sodium azide; triethylamine; In chloroform; N,N-dimethyl-formamide;

DOI:10.1016/j.tetasy.2003.08.019

upstream raw materials:

ethyl (2S,4R)-1-benzyl-4-(4-methylphenylsulfonyloxy)prolinate

trans-4-hydroxy-L-proline ethyl ester hydrochloride

benzyl bromide

(2S,4R)-ethyl N¹-benzyl-4-hydroxypyrrolidine-2-carboxylate

Downstream raw materials:

(2S,4S)-(4-amino-1-benzylpyrrolidin-2-yl)methanol

Refernces