(2R-cis)- and (2R-trans)-4-cyanomethyl-2-(2,4-difluorophenyl)-2-[(1H-pyrrol-1-yl)methyl]tetrahydrofuran

Base Information

• Chemical Name: (2R-cis)- and (2R-trans)-4-cyanomethyl-2-(2,4-difluorophenyl)-2-[(1H-pyrrol-1-yl)methyl]tetrahydrofuran
• CAS No.: 310882-10-1
• Molecular Formula: C₁₇H₁₆F₂N₂O
• Molecular Weight: 302.324

Synonyms:(2R-cis)- and (2R-trans)-4-cyanomethyl-2-(2,4-difluorophenyl)-2-[(1H-pyrrol-1-yl)methyl]tetrahydrofuran

Chemical Property of (2R-cis)- and (2R-trans)-4-cyanomethyl-2-(2,4-difluorophenyl)-2-[(1H-pyrrol-1-yl)methyl]tetrahydrofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of (2R-cis)- and (2R-trans)-4-cyanomethyl-2-(2,4-difluorophenyl)-2-[(1H-pyrrol-1-yl)methyl]tetrahydrofuran

There total 7 articles about (2R-cis)- and (2R-trans)-4-cyanomethyl-2-(2,4-difluorophenyl)-2-[(1H-pyrrol-1-yl)methyl]tetrahydrofuran 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: 97.2%

potassium cyanide (151-50-8) + (2R-cis)- and (2R-trans)-2-(2,4-difluorophenyl)-4-[[(4-methylphenyl)sulfonyloxy]methyl]-2-[(1H-pyrrol-1-yl)methyl]tetrahydrofuran (310882-07-6) → (2R-cis)- and (2R-trans)-4-cyanomethyl-2-(2,4-difluorophenyl)-2-[(1H-pyrrol-1-yl)methyl]tetrahydrofuran (310882-10-1)

Guidance literature:

In dimethyl sulfoxide; at 55 ℃; for 15h;

DOI:10.1016/S0968-0896(00)00177-2

Reference yield:

(S)-(2-(2,4-difluorophenyl)oxiran-2-yl)methanol (141113-37-3) → (2R-cis)- and (2R-trans)-4-cyanomethyl-2-(2,4-difluorophenyl)-2-[(1H-pyrrol-1-yl)methyl]tetrahydrofuran (310882-10-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: NaH / dimethylformamide / 0 - 20 °C

1.2: 46.2 percent / dimethylformamide / 2.5 h / 50 - 60 °C

2.1: Et₃N / CH₂Cl₂ / 2 h / 20 °C

3.1: 2.61 g / NaH / dimethylformamide / 4 h / 20 °C

4.1: NaH; DMSO / 1 h / 20 °C

4.2: 70.2 percent / dimethylsulfoxide / 30 h / 75 - 80 °C

5.1: 88.8 percent / NaBH₄; LiCl / ethanol / 28 h / 20 °C

6.1: 4-(dimethylamino)pyridine; Et₃N / CH₂Cl₂ / 15.5 h / 20 °C

7.1: 2.34 g / NaH / toluene / 4 h / Heating

8.1: 97.2 percent / dimethylsulfoxide / 15 h / 55 °C

With dmap; sodium tetrahydroborate; sodium hydride; dimethyl sulfoxide; triethylamine; lithium chloride; In ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 1.1: deprotonation / 1.2: Ring cleavage / 2.1: mesylation / 3.1: Cyclization / 4.1: Metallation / 4.2: Ring cleavage / 5.1: Reduction / 6.1: Tosylation / 7.1: Cyclization / 8.1: Substitution;

DOI:10.1016/S0968-0896(00)00177-2

Reference yield:

(2R)-2-(2,4-difluorophenyl)-2-[(1H-pyrrol-1-yl)methyl]oxirane → (2R-cis)- and (2R-trans)-4-cyanomethyl-2-(2,4-difluorophenyl)-2-[(1H-pyrrol-1-yl)methyl]tetrahydrofuran (310882-10-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaH; DMSO / 1 h / 20 °C

1.2: 70.2 percent / dimethylsulfoxide / 30 h / 75 - 80 °C

2.1: 88.8 percent / NaBH₄; LiCl / ethanol / 28 h / 20 °C

3.1: 4-(dimethylamino)pyridine; Et₃N / CH₂Cl₂ / 15.5 h / 20 °C

4.1: 2.34 g / NaH / toluene / 4 h / Heating

5.1: 97.2 percent / dimethylsulfoxide / 15 h / 55 °C

With dmap; sodium tetrahydroborate; sodium hydride; dimethyl sulfoxide; triethylamine; lithium chloride; In ethanol; dichloromethane; dimethyl sulfoxide; toluene; 1.1: Metallation / 1.2: Ring cleavage / 2.1: Reduction / 3.1: Tosylation / 4.1: Cyclization / 5.1: Substitution;

DOI:10.1016/S0968-0896(00)00177-2

upstream raw materials:

potassium cyanide

(2R-cis)- and (2R-trans)-2-(2,4-difluorophenyl)-4-[[(4-methylphenyl)sulfonyloxy]methyl]-2-[(1H-pyrrol-1-yl)methyl]tetrahydrofuran

(S)-(2-(2,4-difluorophenyl)oxiran-2-yl)methanol

(2R)-2-(2,4-difluorophenyl)-3-(1H-pyrrol-1-yl)-1,2-propanediol

Downstream raw materials:

(2R-cis)-2-(2,4-difluorophenyl)-4-(5-methyl-4-oxohexyl)-2-[(1H-pyrrol-1-yl)methyl]tetrahydrofuran

6-[(3R,5R)-5-(2,4-Difluoro-phenyl)-5-pyrrol-1-ylmethyl-tetrahydro-furan-3-yl]-2-methyl-hexan-3-one

(2R-cis)- and (2R-trans)-2-(2,4-difluorophenyl)-4-formylmethyl-2-[(1H-pyrrol-1-yl)methyl]tetrahydrofuran

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