methyl (3S)-hydroxy-5-<1,2-diisopropyl-4-(4-fluorophenyl)-1H-pyrrol-3-yl>pent-4(E)-enoate

Base Information

• Chemical Name: methyl (3S)-hydroxy-5-<1,2-diisopropyl-4-(4-fluorophenyl)-1H-pyrrol-3-yl>pent-4(E)-enoate
• CAS No.: 124401-62-3
• Molecular Formula: C₂₂H₂₈FNO₃
• Molecular Weight: 373.468
• Mol file: 124401-62-3.mol

Synonyms:

Chemical Property of methyl (3S)-hydroxy-5-<1,2-diisopropyl-4-(4-fluorophenyl)-1H-pyrrol-3-yl>pent-4(E)-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (3S)-hydroxy-5-<1,2-diisopropyl-4-(4-fluorophenyl)-1H-pyrrol-3-yl>pent-4(E)-enoate

There total 11 articles about methyl (3S)-hydroxy-5-<1,2-diisopropyl-4-(4-fluorophenyl)-1H-pyrrol-3-yl>pent-4(E)-enoate 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:

4-fluoro-β-nitrostyrene (5153-69-5,706-08-1) → methyl (3S)-hydroxy-5-<1,2-diisopropyl-4-(4-fluorophenyl)-1H-pyrrol-3-yl>pent-4(E)-enoate (124401-62-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 49.7 percent / methanol / 48 h

2: 77 percent / lithium aluminum hydride / diethyl ether / 1.) 0 deg C, 1 h, 2.) 20 deg C, 1 h

3: 87 percent / N-methylmorpholine N-oxide, tris(triphenylphosphine)ruthenium(II) dichloride / acetone / 20 h / Ambient temperature

4: 1.) sodium hydride / 1.) THF, 0 deg C, 40 min, 2.) RT, 2 h

5: 1.) 1.2 M diisobutylaluminum hydride, 2.) water / 1a.) THF, toluene, 0 deg C, 1 h, 1b.) RT, 1.5 h, 2.) 1 h

6: 1.) LDA / 1.) THF, 0 deg C, 30 min, 2.) -90 deg C, 2 h

7: methanol / 3 h / Ambient temperature

With lithium aluminium tetrahydride; tris(triphenylphosphine)ruthenium(II) chloride; water; sodium hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; lithium diisopropyl amide; In methanol; diethyl ether; acetone;

DOI:10.1021/jm00163a011

Reference yield:

1-(4-fluorophenyl)-2-nitropropene (134538-46-8,775-31-5) → methyl (3S)-hydroxy-5-<1,2-diisopropyl-4-(4-fluorophenyl)-1H-pyrrol-3-yl>pent-4(E)-enoate (124401-62-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 50 percent / ethanol / 12 h / Heating

2: 1.) NaH / 1a.) toluene, 60 deg C, 30 min, 1b.) 100 deg C, 10 min, 2.) reflux

3: 75 percent / lithium aluminum hydride / tetrahydrofuran / 20 h / Heating

4: 87 percent / N-methylmorpholine N-oxide, tris(triphenylphosphine)ruthenium(II) dichloride / acetone / 20 h / Ambient temperature

5: 1.) sodium hydride / 1.) THF, 0 deg C, 40 min, 2.) RT, 2 h

6: 1.) 1.2 M diisobutylaluminum hydride, 2.) water / 1a.) THF, toluene, 0 deg C, 1 h, 1b.) RT, 1.5 h, 2.) 1 h

7: 1.) LDA / 1.) THF, 0 deg C, 30 min, 2.) -90 deg C, 2 h

8: methanol / 3 h / Ambient temperature

With lithium aluminium tetrahydride; tris(triphenylphosphine)ruthenium(II) chloride; water; sodium hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; lithium diisopropyl amide; In tetrahydrofuran; methanol; ethanol; acetone;

DOI:10.1021/jm00163a011

Reference yield:

4-methyl-3-oxo-N-phenylpentanamide (124401-38-3) → methyl (3S)-hydroxy-5-<1,2-diisopropyl-4-(4-fluorophenyl)-1H-pyrrol-3-yl>pent-4(E)-enoate (124401-62-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 28.9 g / acetic acid / toluene / 16 h / Heating

2: 50 percent / ethanol / 12 h / Heating

3: 1.) NaH / 1a.) toluene, 60 deg C, 30 min, 1b.) 100 deg C, 10 min, 2.) reflux

4: 75 percent / lithium aluminum hydride / tetrahydrofuran / 20 h / Heating

5: 87 percent / N-methylmorpholine N-oxide, tris(triphenylphosphine)ruthenium(II) dichloride / acetone / 20 h / Ambient temperature

6: 1.) sodium hydride / 1.) THF, 0 deg C, 40 min, 2.) RT, 2 h

7: 1.) 1.2 M diisobutylaluminum hydride, 2.) water / 1a.) THF, toluene, 0 deg C, 1 h, 1b.) RT, 1.5 h, 2.) 1 h

8: 1.) LDA / 1.) THF, 0 deg C, 30 min, 2.) -90 deg C, 2 h

9: methanol / 3 h / Ambient temperature

With lithium aluminium tetrahydride; tris(triphenylphosphine)ruthenium(II) chloride; water; sodium hydride; diisobutylaluminium hydride; acetic acid; 4-methylmorpholine N-oxide; lithium diisopropyl amide; In tetrahydrofuran; methanol; ethanol; acetone; toluene;

DOI:10.1021/jm00163a011

upstream raw materials:

4-fluoro-β-nitrostyrene

1-(4-fluorophenyl)-2-nitropropene

4-methyl-3-oxo-N-phenylpentanamide

3-(isopropylamino)-4-methylpent-2(E)-enoic acid anilide

Downstream raw materials:

tert-butyl (5S)-hydroxy-3-oxo-7-<1,2-diisopropyl-4-(4-fluorophenyl)-1H-pyrrol-3-yl>hept-6(E)-enoate

tert-butyl 3(R),5(S)-dihydroxy-7-<1,2-diisopropyl-4-(4-fluorophenyl)-1H-pyrrol-3-yl>hept-6(E)-enoate