(4R)-4-Hydroxy-1-Boc-D-proline ethyl ester

Base Information

• Chemical Name: (4R)-4-Hydroxy-1-Boc-D-proline ethyl ester
• CAS No.: 77450-00-1
• Molecular Formula: C₁₂H₂₁NO₅
• Molecular Weight: 259.302
• DSSTox Substance ID: DTXSID401141281
• Nikkaji Number: J2.990.807I
• Mol file: 77450-00-1.mol

Synonyms:77450-00-1;(4R)-4-Hydroxy-1-Boc-D-proline ethyl ester;SCHEMBL2682785;MNMDZSAWTQOEHX-RKDXNWHRSA-;MNMDZSAWTQOEHX-RKDXNWHRSA-N;DTXSID401141281;(4R)-4-Hydroxy-1-Boc-D-prolineethylester;CS-0434697;F79655;(2R,4R)-1-tert-Butyl 2-ethyl 4-hydroxypyrrolidine-1,2-dicarboxylate;1-O-tert-butyl 2-O-ethyl (2R,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate;1-tert-Butyl 2-ethyl (2R,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate;(2R-cis)-4-Hydroxy-1,2-pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) 2-ethyl ester;1-(1,1-Dimethylethyl) 2-ethyl (2R,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate;InChI=1/C12H21NO5/c1-5-17-10(15)9-6-8(14)7-13(9)11(16)18-12(2,3)4/h8-9,14H,5-7H2,1-4H3/t8-,9-/m1/s1

Chemical Property of (4R)-4-Hydroxy-1-Boc-D-proline ethyl ester

Chemical Property:

• Boiling Point: 350.2±42.0 °C(Predicted)
• Density: 1.189±0.06 g/cm3(Predicted)
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 259.14197277
• Heavy Atom Count: 18
• Complexity: 323

Purity/Quality:

98.5% ^*data from raw suppliers

(4R)-4-Hydroxy-1-Boc-D-prolineethylester 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1CC(CN1C(=O)OC(C)(C)C)O
• Isomeric SMILES: CCOC(=O)[C@H]1C[C@H](CN1C(=O)OC(C)(C)C)O

Technology Process of (4R)-4-Hydroxy-1-Boc-D-proline ethyl ester

There total 2 articles about (4R)-4-Hydroxy-1-Boc-D-proline ethyl 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:

(S)-ethyl 2-((tert-butoxycarbonyl)(3-chloro-2-hydroxypropyl)amino)acetate → (2R,4R)-4-hydroxyproline-1,2-dicarboxylic acid 1-tert-butyl 2-ethyl ester (77450-00-1) + (2S,4R)-4-hydroxyproline-1,2-dicarboxylic acid 1-tert-butyl 2-ethyl ester (37813-30-2)

Guidance literature:

With lithium hexamethyldisilazane; In N,N-dimethyl-formamide; at -58 - 50 ℃; for 4.66667h; Overall yield = 72%; diastereoselective reaction;

DOI:10.1016/j.tetlet.2015.03.119

Reference yield:

C7H14ClNO3 → (2R,4R)-4-hydroxyproline-1,2-dicarboxylic acid 1-tert-butyl 2-ethyl ester (77450-00-1) + (2S,4R)-4-hydroxyproline-1,2-dicarboxylic acid 1-tert-butyl 2-ethyl ester (37813-30-2)

Guidance literature:

Multi-step reaction with 2 steps

1: isopropyl alcohol / 4 h / Inert atmosphere

2: lithium hexamethyldisilazane / N,N-dimethyl-formamide / 4.67 h / -58 - 50 °C

With lithium hexamethyldisilazane; In N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1016/j.tetlet.2015.03.119

Reference yield: 89.0%

(2R,4R)-4-hydroxyproline-1,2-dicarboxylic acid 1-tert-butyl 2-ethyl ester (77450-00-1) + p-toluenesulfonyl chloride (98-59-9) → N-(tert-Butoxycarbonyl)-allo-4-hydroxy-D-proline Ethyl Ester p-Toluenesulfonate (77450-01-2)

Guidance literature:

In pyridine; 1.) 0 deg C, 1 h, 2.) room temperature, 48 h;

DOI:10.1021/jo00327a023

Downstream raw materials:

N-(tert-Butoxycarbonyl)-allo-4-hydroxy-D-proline Ethyl Ester p-Toluenesulfonate

ethyl (2R,4R)-N-tert-butyloxycarbonyl-4-tert-butyldiphenylsiloxyprolinate

(4R)-1-(tert-butoxycarbonyl)-4-hydroxy-D-proline

(2R)-N-Boc-trans-4-hydroxy-D-proline tert-butyl ester