(4S,5R)-Methyl 4-hydroxy-4,5-dihydro-1H-pyrazole-5-carboxylate

Base Information

• Chemical Name: (4S,5R)-Methyl 4-hydroxy-4,5-dihydro-1H-pyrazole-5-carboxylate
• CAS No.: 323196-50-5
• Molecular Formula: C₅H₈N₂O₃
• Molecular Weight: 144.13
• DSSTox Substance ID: DTXSID601179553
• Nikkaji Number: J1.424.786F
• Mol file: 323196-50-5.mol

Synonyms:323196-50-5;(4S,5R)-Methyl 4-hydroxy-4,5-dihydro-1H-pyrazole-5-carboxylate;DTXSID601179553;Methyl (4S,5R)-4,5-dihydro-4-hydroxy-1H-pyrazole-5-carboxylate

Chemical Property of (4S,5R)-Methyl 4-hydroxy-4,5-dihydro-1H-pyrazole-5-carboxylate

Chemical Property:

• XLogP3: -0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 144.05349212
• Heavy Atom Count: 10
• Complexity: 168

Purity/Quality:

(4S,5R)-4,5-dihydro-4-hydroxy-1H-Pyrazole-5-carboxylicacidmethylester 97.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C1C(C=NN1)O
• Isomeric SMILES: COC(=O)[C@H]1[C@@H](C=NN1)O

Technology Process of (4S,5R)-Methyl 4-hydroxy-4,5-dihydro-1H-pyrazole-5-carboxylate

There total 4 articles about (4S,5R)-Methyl 4-hydroxy-4,5-dihydro-1H-pyrazole-5-carboxylate 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: 70.0%

(2R,3S)-2-Hydrazino-3-hydroxy-4,4-dimethoxy-butyric acid methyl ester (323196-51-6) → (4S,5R)-5-carbomethoxy-4-hydroxy-Δ2-pyrazoline (323196-50-5)

Guidance literature:

With trifluoroacetic acid; at 20 ℃; for 2h;

DOI:10.1016/S0040-4039(00)01582-3

Reference yield:

4,4-dimethoxy-3-oxo-butyric acid methyl ester (60705-25-1) → (4S,5R)-5-carbomethoxy-4-hydroxy-Δ2-pyrazoline (323196-50-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / [(R)-Binap RuCl₂]2; Et₃N / methanol / 18 h / 65 °C

2: 66 percent / LDA / tetrahydrofuran / -78 °C

3: 100 percent / H₂ / Pd/C / methanol / 1 h / 20 °C

4: 70 percent / TFA / 2 h / 20 °C

With [(R)-Binap RuCl₂]2; hydrogen; triethylamine; trifluoroacetic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; 1: Reduction / 2: Addition / 3: Hydrogenolysis / 4: Cyclization;

DOI:10.1016/S0040-4039(00)01582-3

Reference yield:

(S)-3-Hydroxy-4,4-dimethoxy-butyric acid methyl ester (323201-62-3) → (4S,5R)-5-carbomethoxy-4-hydroxy-Δ2-pyrazoline (323196-50-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 66 percent / LDA / tetrahydrofuran / -78 °C

2: 100 percent / H₂ / Pd/C / methanol / 1 h / 20 °C

3: 70 percent / TFA / 2 h / 20 °C

With hydrogen; trifluoroacetic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; 1: Addition / 2: Hydrogenolysis / 3: Cyclization;

DOI:10.1016/S0040-4039(00)01582-3

upstream raw materials:

(2R,3S)-2-Hydrazino-3-hydroxy-4,4-dimethoxy-butyric acid methyl ester

4,4-dimethoxy-3-oxo-butyric acid methyl ester

(S)-3-Hydroxy-4,4-dimethoxy-butyric acid methyl ester

C₂₃H₂₈N₂O₉