ethyl (αξ,βξ)-β-hydroxy-α-methyl-α-<(ξ)-2-methylenecyclopentyl>-1-(phenylsulfonyl)-1H-pyrrole-3-propanoate

Base Information

• Chemical Name: ethyl (αξ,βξ)-β-hydroxy-α-methyl-α-<(ξ)-2-methylenecyclopentyl>-1-(phenylsulfonyl)-1H-pyrrole-3-propanoate
• CAS No.: 157331-38-9
• Molecular Formula: C₂₂H₂₇NO₅S
• Molecular Weight: 417.526
• Mol file: 157331-38-9.mol

Synonyms:ethyl (αξ,βξ)-β-hydroxy-α-methyl-α-<(ξ)-2-methylenecyclopentyl>-1-(phenylsulfonyl)-1H-pyrrole-3-propanoate

Chemical Property of ethyl (αξ,βξ)-β-hydroxy-α-methyl-α-<(ξ)-2-methylenecyclopentyl>-1-(phenylsulfonyl)-1H-pyrrole-3-propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (αξ,βξ)-β-hydroxy-α-methyl-α-<(ξ)-2-methylenecyclopentyl>-1-(phenylsulfonyl)-1H-pyrrole-3-propanoate

There total 2 articles about ethyl (αξ,βξ)-β-hydroxy-α-methyl-α-<(ξ)-2-methylenecyclopentyl>-1-(phenylsulfonyl)-1H-pyrrole-3-propanoate 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:

Triethyl orthopropionate (115-80-0) → ethyl (αξ,βξ)-β-hydroxy-α-methyl-α-<(ξ)-2-methylenecyclopentyl>-1-(phenylsulfonyl)-1H-pyrrole-3-propanoate (157331-38-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / pivalic acid / 3 h / 130 °C

2: 1.) lithium diisopropylamide / 1.) THF, -82 deg C to -69 deg C, 45 min, 2.) THF, -69 deg C to -59 deg C, 1 h

With lithium diisopropyl amide; Trimethylacetic acid;

DOI:10.1248/cpb.42.846

Reference yield:

1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde (88075-95-0) + ethyl α-methyl-2-methylene-1-cyclopentaneacetate (157331-37-8) → ethyl (αξ,βξ)-β-hydroxy-α-methyl-α-<(ξ)-2-methylenecyclopentyl>-1-(phenylsulfonyl)-1H-pyrrole-3-propanoate (157331-38-9)

Guidance literature:

With lithium diisopropyl amide; Yield given. Multistep reaction; 1.) THF, -82 deg C to -69 deg C, 45 min, 2.) THF, -69 deg C to -59 deg C, 1 h;

DOI:10.1248/cpb.42.846

Reference yield: 84.0%

ethyl (αξ,βξ)-β-hydroxy-α-methyl-α-<(ξ)-2-methylenecyclopentyl>-1-(phenylsulfonyl)-1H-pyrrole-3-propanoate (157331-38-9) → ethyl (αξ)-α-methyl-α-<(ξ)-2-methylenecyclopentyl>-β-oxo-1-(phenylsulfonyl)-1H-pyrrole-3-propanoate (157331-40-3)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; for 2h; Heating;

DOI:10.1248/cpb.42.846

upstream raw materials:

1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde

ethyl α-methyl-2-methylene-1-cyclopentaneacetate

Triethyl orthopropionate

Downstream raw materials:

ethyl (αξ)-α-methyl-α-<(ξ)-2-methylenecyclopentyl>-β-oxo-1-(phenylsulfonyl)-1H-pyrrole-3-propanoate

4-butyl-5-methyl-1-(phenylsulfonyl)-1,6,7,8-tetrahydrocyclopentindole

4-(3-butenyl)-5-methyl-1-(phenylsulfonyl)-1,6,7,8-tetrahydrocyclopentindole

4-<(E)-1-butenyl>-5-methyl-1-(phenylsulfonyl)-1,6,7,8-tetrahydrocyclopentindole