BOC-4-HYDROXY-L-PYRROLIDINE LACTONE

Base Information

• Chemical Name: BOC-4-HYDROXY-L-PYRROLIDINE LACTONE
• CAS No.: 113775-22-7
• Molecular Formula: C₁₀H₁₅NO₄
• Molecular Weight: 213.233
• Hs Code.: 2933998090
• Mol file: 113775-22-7.mol

Synonyms:2-Oxa-5-azabicyclo[2.2.1]heptane-5-carboxylicacid, 3-oxo-, 1,1-dimethylethyl ester, (1S)-; tert-Butyl(1S,4S)-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate

Chemical Property of BOC-4-HYDROXY-L-PYRROLIDINE LACTONE

Chemical Property:

• Vapor Pressure: 4.63E-05mmHg at 25°C
• Melting Point: 109-114°C
• Boiling Point: 349.7°C at 760 mmHg
• PKA: -1.25±0.20(Predicted)
• Flash Point: 165.3°C
• PSA: 55.84000
• Density: 1.246g/cm³
• LogP: 0.85910
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

98%min ^*data from raw suppliers

Boc-4-Hydroxy-L-pyrrolidineLactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of BOC-4-HYDROXY-L-PYRROLIDINE LACTONE

There total 10 articles about BOC-4-HYDROXY-L-PYRROLIDINE LACTONE 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: 97.0%

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid (13726-69-7,946610-68-0) → 2’-methyl-2’-propanyl (1S,4S)-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate (87250-97-3,113775-22-7)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 20h;

DOI:10.1016/j.bmc.2007.01.001

Reference yield: 62.0%

di-tert-butyl dicarbonate (24424-99-5) + 4R-4-hydroxyproline (51-35-4,30724-02-8) → 2’-methyl-2’-propanyl (1S,4S)-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate (87250-97-3,113775-22-7)

Guidance literature:

di-tert-butyl dicarbonate; 4R-4-hydroxyproline; With potassium carbonate; In 1,4-dioxane; at 0 - 20 ℃; for 8h;

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 ℃; for 4h;

DOI:10.1002/anie.200903477

Reference yield: 18.0%

di-tert-butyl dicarbonate (24424-99-5) + C12H15NO3 → 2’-methyl-2’-propanyl (1S,4S)-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate (87250-97-3,113775-22-7) + N-(tert-butoxycarbonyl)-(2S,4R)-4-hydroxyproline benzyl ester (89813-47-8)

Guidance literature:

With triethylamine; In 1,4-dioxane;

DOI:10.1039/c3ra45184d

upstream raw materials:

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

(2S,4R)-1-(tert-butoxycarbonyl)-4-[(methylsulfonyl)oxy]-2-pyrrolidinecarboxylic acid

di-tert-butyl dicarbonate

4R-4-hydroxyproline

Downstream raw materials:

C₂₉H₄₄N₄O₈SSi

Refernces

• 1、 Lu, Jin-Yong,Riedrich, Matthias,Mikyna, Martin,Arndt, Hans-Dieter. "Aza-wittig-supported synthesis of the a ring of nosiheptide". . p. 8137 - 8140. Retrieved 2009.
• 2、 Morgan, Timaeus E. F.,Riley, Leanne M.,Tavares, Adriana A. S.,Sutherland, Andrew. "Automated Radiosynthesis of cis- And trans-4-[18F]Fluoro- l -proline Using [18F]Fluoride". . p. 14054 - 14060. Retrieved 2021/05/29.