(2E)-2-[(2S)-2-(2-hydroxypropan-2-yl)-3,4-dihydro-2H-pyrrol-5-yl]-2-[(5S)-5-(2-hydroxypropan-2-yl)pyrrolidin-2-ylidene]acetonitrile

Base Information

• Chemical Name: (2E)-2-[(2S)-2-(2-hydroxypropan-2-yl)-3,4-dihydro-2H-pyrrol-5-yl]-2-[(5S)-5-(2-hydroxypropan-2-yl)pyrrolidin-2-ylidene]acetonitrile
• CAS No.: 105251-53-4
• Molecular Formula: C₁₆H₂₅N₃O₂
• Molecular Weight: 291.393
• DSSTox Substance ID: DTXSID601101552
• Mol file: 105251-53-4.mol

Synonyms:DTXSID601101552;105251-53-4;2H-Pyrrole-5-acetonitrile, 3,4-dihydro-2-(1-hydroxy-1-methylethyl)-alpha-[5-(1-hydroxy-1-methylethyl)-2-pyrrolidinylidene]-, [S-[R*,R*-(E)]]-

Chemical Property of (2E)-2-[(2S)-2-(2-hydroxypropan-2-yl)-3,4-dihydro-2H-pyrrol-5-yl]-2-[(5S)-5-(2-hydroxypropan-2-yl)pyrrolidin-2-ylidene]acetonitrile

Chemical Property:

• XLogP3: 0.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 291.19467705
• Heavy Atom Count: 21
• Complexity: 537

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C1CCC(=C(C#N)C2=NC(CC2)C(C)(C)O)N1)O
• Isomeric SMILES: CC(C)([C@@H]1CC/C(=C(\C#N)/C2=N[C@@H](CC2)C(C)(C)O)/N1)O

Technology Process of (2E)-2-[(2S)-2-(2-hydroxypropan-2-yl)-3,4-dihydro-2H-pyrrol-5-yl]-2-[(5S)-5-(2-hydroxypropan-2-yl)pyrrolidin-2-ylidene]acetonitrile

There total 7 articles about (2E)-2-[(2S)-2-(2-hydroxypropan-2-yl)-3,4-dihydro-2H-pyrrol-5-yl]-2-[(5S)-5-(2-hydroxypropan-2-yl)pyrrolidin-2-ylidene]acetonitrile 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: 76.0%

methylmagnesium bromide (75-16-1) + (1S,9S)-dimethyl 5-cyanosemicorrin-1,9-dicarboxylate (105251-49-8) → (1S,9S)-1,9-bis(1-hydroxy-1-methylethyl)semicorrin-5-carbonitrile (105251-53-4)

Guidance literature:

In diethyl ether; at 23 ℃;

Reference yield:

(2S)-methyl 5-ethoxy-3,4-dihydro-2H-pyrrol-2-carboxylate (65571-69-9) → (1S,9S)-1,9-bis(1-hydroxy-1-methylethyl)semicorrin-5-carbonitrile (105251-53-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 81 percent / 23 h / 100 °C

2: CF₃CO₂H / 0.13 h / 23 °C

3: 75 percent / CF₃CO₂H / 1,2-dichloro-ethane / 4.5 h / 65 °C

4: 76 percent / diethyl ether / 1.) 0.5 h, 0 deg C; 2.) 2 h, 23 deg C

With trifluoroacetic acid; In diethyl ether; 1,2-dichloro-ethane;

DOI:10.1002/hlca.19880710620

Reference yield:

methyl (S)-pyroglutamate (4931-66-2) → (1S,9S)-1,9-bis(1-hydroxy-1-methylethyl)semicorrin-5-carbonitrile (105251-53-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / CH₂Cl₂ / 5 h / Heating

2: 81 percent / 23 h / 100 °C

3: CF₃CO₂H / 0.13 h / 23 °C

4: 75 percent / CF₃CO₂H / 1,2-dichloro-ethane / 4.5 h / 65 °C

5: 76 percent / diethyl ether / 1.) 0.5 h, 0 deg C; 2.) 2 h, 23 deg C

With trifluoroacetic acid; In diethyl ether; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1002/hlca.19880710620

upstream raw materials:

methylmagnesium bromide

(1S,9S)-dimethyl 5-cyanosemicorrin-1,9-dicarboxylate

(2S)-methyl 5-(cyanomethylidene)pyrrolidine-2-carboxylate

(2S)-methyl 5-<<(tert-butyl)oxycarbonyl>(cyano)methylidene>pyrrolidine-2-carboxylate