(2R,4R)-1-allyloxycarbonyl-4-benzoylthio-2-[(5-hydroxymethyl-1-methylpyrazol-4-yl)methyl]pyrrolidine

Base Information

• Chemical Name: (2R,4R)-1-allyloxycarbonyl-4-benzoylthio-2-[(5-hydroxymethyl-1-methylpyrazol-4-yl)methyl]pyrrolidine
• CAS No.: 164162-17-8
• Molecular Formula: C₂₁H₂₅N₃O₄S
• Molecular Weight: 415.513
• Mol file: 164162-17-8.mol

Synonyms:(2R,4R)-1-allyloxycarbonyl-4-benzoylthio-2-[(5-hydroxymethyl-1-methylpyrazol-4-yl)methyl]pyrrolidine

Chemical Property of (2R,4R)-1-allyloxycarbonyl-4-benzoylthio-2-[(5-hydroxymethyl-1-methylpyrazol-4-yl)methyl]pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4R)-1-allyloxycarbonyl-4-benzoylthio-2-[(5-hydroxymethyl-1-methylpyrazol-4-yl)methyl]pyrrolidine

There total 15 articles about (2R,4R)-1-allyloxycarbonyl-4-benzoylthio-2-[(5-hydroxymethyl-1-methylpyrazol-4-yl)methyl]pyrrolidine 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:

(1-methyl-1H-pyrazol-5-yl)methanol (84547-61-5) → (2R,4R)-1-allyloxycarbonyl-4-benzoylthio-2-[(5-hydroxymethyl-1-methylpyrazol-4-yl)methyl]pyrrolidine (164162-17-8)

Guidance literature:

Multi-step reaction with 13 steps

1: 22.26 g / imidazole / dimethylformamide / 20 °C

2: 10.81 g / Br₂; Na₂CO₃ / CH₂Cl₂ / 2 h / 0 - 20 °C

3: 44 percent / n-BuLi / tetrahydrofuran; hexane / 3 h / -70 - 5 °C

4: HCO₂NH₄ / Pd/C / methanol / 0.67 h / Heating

5: 6.39 g / aq. NaOH / tetrahydrofuran / 0.17 h / 0 - 5 °C / pH 8.5 - 10

6: NaH / tetrahydrofuran / 0.5 h / 0 - 8 °C

7: tetrahydrofuran / 5 h / 0 - 20 °C

8: 3.47 g / AIBN; n-Bu₃SnH / toluene / 0.5 h / Heating

9: 83 percent / aq. HCl / acetonitrile / 2 h / 20 °C

10: 58 percent / DMAP / CH₂Cl₂ / 0 °C

11: Et₃N / CH₂Cl₂ / 2 h / 5 °C

12: 1.10 g / aq. HCl / acetonitrile / 2 h / 20 °C

13: 1.08 g / t-BuOK / dimethylformamide / 2.3 h / 80 °C

With 1H-imidazole; hydrogenchloride; dmap; sodium hydroxide; n-butyllithium; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; bromine; tri-n-butyl-tin hydride; ammonium formate; sodium hydride; sodium carbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0968-0896(00)00314-X

Reference yield:

5-tert-butyldimethylsilyloxymethyl-1-methylpyrazole (351529-85-6) → (2R,4R)-1-allyloxycarbonyl-4-benzoylthio-2-[(5-hydroxymethyl-1-methylpyrazol-4-yl)methyl]pyrrolidine (164162-17-8)

Guidance literature:

Multi-step reaction with 12 steps

1: 10.81 g / Br₂; Na₂CO₃ / CH₂Cl₂ / 2 h / 0 - 20 °C

2: 44 percent / n-BuLi / tetrahydrofuran; hexane / 3 h / -70 - 5 °C

3: HCO₂NH₄ / Pd/C / methanol / 0.67 h / Heating

4: 6.39 g / aq. NaOH / tetrahydrofuran / 0.17 h / 0 - 5 °C / pH 8.5 - 10

5: NaH / tetrahydrofuran / 0.5 h / 0 - 8 °C

6: tetrahydrofuran / 5 h / 0 - 20 °C

7: 3.47 g / AIBN; n-Bu₃SnH / toluene / 0.5 h / Heating

8: 83 percent / aq. HCl / acetonitrile / 2 h / 20 °C

9: 58 percent / DMAP / CH₂Cl₂ / 0 °C

10: Et₃N / CH₂Cl₂ / 2 h / 5 °C

11: 1.10 g / aq. HCl / acetonitrile / 2 h / 20 °C

12: 1.08 g / t-BuOK / dimethylformamide / 2.3 h / 80 °C

With hydrogenchloride; dmap; sodium hydroxide; n-butyllithium; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; bromine; tri-n-butyl-tin hydride; ammonium formate; sodium hydride; sodium carbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0968-0896(00)00314-X

Reference yield:

4-bromo-5-tert-butyldimethylsilyloxymethyl-1-methylpyrazole (164162-09-8) → (2R,4R)-1-allyloxycarbonyl-4-benzoylthio-2-[(5-hydroxymethyl-1-methylpyrazol-4-yl)methyl]pyrrolidine (164162-17-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 44 percent / n-BuLi / tetrahydrofuran; hexane / 3 h / -70 - 5 °C

2: HCO₂NH₄ / Pd/C / methanol / 0.67 h / Heating

3: 6.39 g / aq. NaOH / tetrahydrofuran / 0.17 h / 0 - 5 °C / pH 8.5 - 10

4: NaH / tetrahydrofuran / 0.5 h / 0 - 8 °C

5: tetrahydrofuran / 5 h / 0 - 20 °C

6: 3.47 g / AIBN; n-Bu₃SnH / toluene / 0.5 h / Heating

7: 83 percent / aq. HCl / acetonitrile / 2 h / 20 °C

8: 58 percent / DMAP / CH₂Cl₂ / 0 °C

9: Et₃N / CH₂Cl₂ / 2 h / 5 °C

10: 1.10 g / aq. HCl / acetonitrile / 2 h / 20 °C

11: 1.08 g / t-BuOK / dimethylformamide / 2.3 h / 80 °C

With hydrogenchloride; dmap; sodium hydroxide; n-butyllithium; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; tri-n-butyl-tin hydride; ammonium formate; sodium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0968-0896(00)00314-X

upstream raw materials:

(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-[5-(tert-butyl-dimethyl-silanyloxymethyl)-1-methyl-1H-pyrazol-4-ylmethyl]-pyrrolidine-1-carboxylic acid allyl ester

(2R,4R)-1-allyloxycarbonyl-2-(5-hydroxymethyl-1-methylpyrazol-4-yl)methyl-4-methanesulfonyloxypyrrolidine

thiobenzoic acid

(2R,4R)-1-allyloxycarbonyl-4-hydroxy-2-[(5-hydroxymethyl-1-methylpyrazol-4-yl)methyl]pyrrolidine