benzyl 4-methyl-3-((R)-2,2,2-trifluoro-1-hydroxyethyl)pyrrole-2-carboxylate

Base Information

• Chemical Name: benzyl 4-methyl-3-((R)-2,2,2-trifluoro-1-hydroxyethyl)pyrrole-2-carboxylate
• CAS No.: 220802-59-5
• Molecular Formula: C₁₅H₁₄F₃NO₃
• Molecular Weight: 313.276
• Mol file: 220802-59-5.mol

Synonyms:benzyl 4-methyl-3-((R)-2,2,2-trifluoro-1-hydroxyethyl)pyrrole-2-carboxylate

Chemical Property of benzyl 4-methyl-3-((R)-2,2,2-trifluoro-1-hydroxyethyl)pyrrole-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 4-methyl-3-((R)-2,2,2-trifluoro-1-hydroxyethyl)pyrrole-2-carboxylate

There total 10 articles about benzyl 4-methyl-3-((R)-2,2,2-trifluoro-1-hydroxyethyl)pyrrole-2-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:

benzyl 3,5-dimethylpyrrole-2-carboxylate (40236-19-9) → benzyl 4-methyl-3-((R)-2,2,2-trifluoro-1-hydroxyethyl)pyrrole-2-carboxylate (220802-59-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 78 percent / ZnCl₂

2.1: 98 percent / Dess-Martin reagent / CH₂Cl₂ / 30 h / 20 °C

3.1: 99 percent / catecholborane; (S)-5,5-diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine / tetrahydrofuran / 24 h / -30 °C

4.1: 95 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 1.5 h / 20 °C

5.1: SO₂Cl₂ / CH₂Cl₂; diethyl ether / 1.5 h / 20 °C

5.2: 99 percent / H₂O / acetone / 0.67 h / Heating

6.1: 75 percent / diethyl ether / 20 °C

7.1: 98 percent / H₂ / Pd-C / tetrahydrofuran

8.1: 77 percent / I₂; NaI; NaHCO₃ / H₂O; 1,2-dichloro-ethane / 0.67 h / Heating

9.1: 97 percent / H₂; sodium acetate / PtO₂ / methanol

10.1: NaN(Si(CH₃)3)2 / tetrahydrofuran / 0.08 h / 80 °C

With dmap; sulfuryl dichloride; hydrogen; iodine; sodium acetate; sodium hexamethyldisilazane; sodium hydrogencarbonate; Dess-Martin periodane; sodium iodide; zinc(II) chloride; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane;

DOI:10.1016/S0040-4020(01)00780-3

Reference yield:

benzyl 4-(1-hydroxy-2,2,2-trifluoroethyl)-3,5-dimethylpyrrole-2-carboxylate (184775-08-4) → benzyl 4-methyl-3-((R)-2,2,2-trifluoro-1-hydroxyethyl)pyrrole-2-carboxylate (220802-59-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 98 percent / Dess-Martin reagent / CH₂Cl₂ / 30 h / 20 °C

2.1: 99 percent / catecholborane; (S)-5,5-diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine / tetrahydrofuran / 24 h / -30 °C

3.1: 95 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 1.5 h / 20 °C

4.1: SO₂Cl₂ / CH₂Cl₂; diethyl ether / 1.5 h / 20 °C

4.2: 99 percent / H₂O / acetone / 0.67 h / Heating

5.1: 75 percent / diethyl ether / 20 °C

6.1: 98 percent / H₂ / Pd-C / tetrahydrofuran

7.1: 77 percent / I₂; NaI; NaHCO₃ / H₂O; 1,2-dichloro-ethane / 0.67 h / Heating

8.1: 97 percent / H₂; sodium acetate / PtO₂ / methanol

9.1: NaN(Si(CH₃)3)2 / tetrahydrofuran / 0.08 h / 80 °C

With dmap; sulfuryl dichloride; hydrogen; iodine; sodium acetate; sodium hexamethyldisilazane; sodium hydrogencarbonate; Dess-Martin periodane; sodium iodide; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane;

DOI:10.1016/S0040-4020(01)00780-3

Reference yield:

benzyl 3,5-dimethyl-4-((R)-2,2,2-trifluoro-1-hydroxyethyl)pyrrole-2-carboxylate (205492-41-7) → benzyl 4-methyl-3-((R)-2,2,2-trifluoro-1-hydroxyethyl)pyrrole-2-carboxylate (220802-59-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 95 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 1.5 h / 20 °C

2.1: SO₂Cl₂ / CH₂Cl₂; diethyl ether / 1.5 h / 20 °C

2.2: 99 percent / H₂O / acetone / 0.67 h / Heating

3.1: 75 percent / diethyl ether / 20 °C

4.1: 98 percent / H₂ / Pd-C / tetrahydrofuran

5.1: 77 percent / I₂; NaI; NaHCO₃ / H₂O; 1,2-dichloro-ethane / 0.67 h / Heating

6.1: 97 percent / H₂; sodium acetate / PtO₂ / methanol

7.1: NaN(Si(CH₃)3)2 / tetrahydrofuran / 0.08 h / 80 °C

With dmap; sulfuryl dichloride; hydrogen; iodine; sodium acetate; sodium hexamethyldisilazane; sodium hydrogencarbonate; sodium iodide; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane;

DOI:10.1016/S0040-4020(01)00780-3

upstream raw materials:

benzyl alcohol

methyl 3-((R)-1-acetoxy-2,2,2-trifluoroethyl)-4-methylpyrrole-2-carboxylate

benzyl 3,5-dimethylpyrrole-2-carboxylate

benzyl 4-(1-hydroxy-2,2,2-trifluoroethyl)-3,5-dimethylpyrrole-2-carboxylate

Downstream raw materials:

dibenzyl (3S,4'R)-4,3'-dimethyl-3,4'-bis(2,2,2-trifluoro-1-hydroxyethyl)-2,2'-dipyrrylmethane-5,5'-dicarboxylate