ethyl [1-[1-(tert-butoxycarbonyl)-(4R)-methoxy-(2S)-pyrrolidinylcarbony]-4-piperidinyl]acetate

Base Information

• Chemical Name: ethyl [1-[1-(tert-butoxycarbonyl)-(4R)-methoxy-(2S)-pyrrolidinylcarbony]-4-piperidinyl]acetate
• CAS No.: 886447-79-6
• Molecular Formula: C₂₀H₃₄N₂O₆
• Molecular Weight: 398.5
• Mol file: 886447-79-6.mol

Synonyms:ethyl [1-[1-(tert-butoxycarbonyl)-(4R)-methoxy-(2S)-pyrrolidinylcarbony]-4-piperidinyl]acetate

Chemical Property of ethyl [1-[1-(tert-butoxycarbonyl)-(4R)-methoxy-(2S)-pyrrolidinylcarbony]-4-piperidinyl]acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl [1-[1-(tert-butoxycarbonyl)-(4R)-methoxy-(2S)-pyrrolidinylcarbony]-4-piperidinyl]acetate

There total 1 articles about ethyl [1-[1-(tert-butoxycarbonyl)-(4R)-methoxy-(2S)-pyrrolidinylcarbony]-4-piperidinyl]acetate 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: 44.0%

ethyl (piperidin-4-yl)acetate (59184-90-6) + (2S,4R)-1-(tert-butoxycarbonyl)-4-methoxypyrrolidine-2-carboxylic acid (83624-01-5) → ethyl [1-[1-(tert-butoxycarbonyl)-(4R)-methoxy-(2S)-pyrrolidinylcarbony]-4-piperidinyl]acetate (886447-79-6)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1016/j.bmc.2005.11.058

Reference yield:

ethyl [1-[1-(tert-butoxycarbonyl)-(4R)-methoxy-(2S)-pyrrolidinylcarbony]-4-piperidinyl]acetate (886447-79-6) → [1-((2S,4R)-4-Methoxy-1-{2-[3-methoxy-4-(3-o-tolyl-ureido)-phenyl]-acetyl}-pyrrolidine-2-carbonyl)-piperidin-4-yl]-acetic acid

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / TFA / CH₂Cl₂ / 12 h / 20 °C

2: 94 percent / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide HCl salt; HOBt; Et₃N / tetrahydrofuran / 12 h / 20 °C

3: 50 percent / NaOH / tetrahydrofuran; methanol / 5 h / Heating

With sodium hydroxide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/j.bmc.2005.11.058

Reference yield:

ethyl [1-[1-(tert-butoxycarbonyl)-(4R)-methoxy-(2S)-pyrrolidinylcarbony]-4-piperidinyl]acetate (886447-79-6) → ethyl [1-[(4R)-methoxy-1-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl]-(2S)-pyrrolidinylcarbonyl]-4-piperidinyl]acetate (886447-59-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / TFA / CH₂Cl₂ / 12 h / 20 °C

2: 94 percent / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide HCl salt; HOBt; Et₃N / tetrahydrofuran / 12 h / 20 °C

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.bmc.2005.11.058

upstream raw materials:

ethyl (piperidin-4-yl)acetate

(2S,4R)-1-(tert-butoxycarbonyl)-4-methoxypyrrolidine-2-carboxylic acid

Downstream raw materials:

ethyl [1-[(4R)-methoxy-1-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl]-(2S)-pyrrolidinylcarbonyl]-4-piperidinyl]acetate