[(4-{(2R)-2-[(1E)-3-hydroxy-4-phenylbut-1-enyl]-5-oxopyrrolidin-1-yl}butyl)thio]acetonitrile

Base Information

• Chemical Name: [(4-{(2R)-2-[(1E)-3-hydroxy-4-phenylbut-1-enyl]-5-oxopyrrolidin-1-yl}butyl)thio]acetonitrile
• CAS No.: 540721-72-0
• Molecular Formula: C₂₀H₂₆N₂O₂S
• Molecular Weight: 358.505
• Mol file: 540721-72-0.mol

Synonyms:[(4-{(2R)-2-[(1E)-3-hydroxy-4-phenylbut-1-enyl]-5-oxopyrrolidin-1-yl}butyl)thio]acetonitrile

Chemical Property of [(4-{(2R)-2-[(1E)-3-hydroxy-4-phenylbut-1-enyl]-5-oxopyrrolidin-1-yl}butyl)thio]acetonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(4-{(2R)-2-[(1E)-3-hydroxy-4-phenylbut-1-enyl]-5-oxopyrrolidin-1-yl}butyl)thio]acetonitrile

There total 7 articles about [(4-{(2R)-2-[(1E)-3-hydroxy-4-phenylbut-1-enyl]-5-oxopyrrolidin-1-yl}butyl)thio]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: 94.0%

(5R)-5-[(1E)-3-hydroxy-4-phenylbut-1-enyl]-1-{4-[(triisopropylsilyl)thio]butyl}-pyrrolidin-2-one (540721-69-5) + cyanomethyl bromide (590-17-0) → [(4-{(2R)-2-[(1E)-3-hydroxy-4-phenylbut-1-enyl]-5-oxopyrrolidin-1-yl}butyl)thio]acetonitrile (540721-72-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/S0960-894X(03)00042-8

Reference yield:

(R)-5-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidin-2-one (128899-30-9,100548-49-0,106191-02-0) → [(4-{(2R)-2-[(1E)-3-hydroxy-4-phenylbut-1-enyl]-5-oxopyrrolidin-1-yl}butyl)thio]acetonitrile (540721-72-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: NaH / dimethylformamide / 50 °C

1.2: 87 percent / Bu₄NI / dimethylformamide / 50 °C

2.1: 90 percent / HF*Py / CH₂Cl₂

3.1: 95 percent / Dess-Martin periodinane / CH₂Cl₂

4.1: NaH / 1,2-dimethoxy-ethane / 0 °C

4.2: 62 percent / 1,2-dimethoxy-ethane / 20 °C

5.1: 90 percent / NaBH₄ / ethanol / -20 °C

6.1: 85 percent / MeONa; Bu₄NI / dimethylformamide / 50 °C

7.1: 94 percent / nBu₄NF / tetrahydrofuran / 20 °C

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; N,N-dimethyl-formamide; 4.2: Wittig reaction;

DOI:10.1016/S0960-894X(03)00042-8

Reference yield:

(2R)-1-(4-chlorobutyl)-5-oxopyrrolidine-2-carboxaldehyde (540721-67-3) → [(4-{(2R)-2-[(1E)-3-hydroxy-4-phenylbut-1-enyl]-5-oxopyrrolidin-1-yl}butyl)thio]acetonitrile (540721-72-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: NaH / 1,2-dimethoxy-ethane / 0 °C

1.2: 62 percent / 1,2-dimethoxy-ethane / 20 °C

2.1: 90 percent / NaBH₄ / ethanol / -20 °C

3.1: 85 percent / MeONa; Bu₄NI / dimethylformamide / 50 °C

4.1: 94 percent / nBu₄NF / tetrahydrofuran / 20 °C

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; N,N-dimethyl-formamide; 1.2: Wittig reaction;

DOI:10.1016/S0960-894X(03)00042-8

upstream raw materials:

(5R)-5-[(1E)-3-hydroxy-4-phenylbut-1-enyl]-1-{4-[(triisopropylsilyl)thio]butyl}-pyrrolidin-2-one

cyanomethyl bromide

(R)-5-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidin-2-one

(2R)-1-(4-chlorobutyl)-5-oxopyrrolidine-2-carboxaldehyde