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

Base Information

• Chemical Name: (5R)-5-[(1E)-3-hydroxy-4-phenylbut-1-enyl]-1-{4-[(triisopropylsilyl)thio]butyl}-pyrrolidin-2-one
• CAS No.: 540721-69-5
• Molecular Formula: C₂₇H₄₅NO₂SSi
• Molecular Weight: 475.811
• Mol file: 540721-69-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about (5R)-5-[(1E)-3-hydroxy-4-phenylbut-1-enyl]-1-{4-[(triisopropylsilyl)thio]butyl}-pyrrolidin-2-one 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: 85.0%

triisopropylsilanethiol (156275-96-6) + (5R)-1-(4-chlorobutyl)-5-[(1E)-3-hydroxy-4-phenylbut-1-enyl]-pyrrolidin-2-one (540721-64-0) → (5R)-5-[(1E)-3-hydroxy-4-phenylbut-1-enyl]-1-{4-[(triisopropylsilyl)thio]butyl}-pyrrolidin-2-one (540721-69-5)

Guidance literature:

With sodium methylate; tetra-(n-butyl)ammonium iodide; In N,N-dimethyl-formamide; at 50 ℃;

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) → (5R)-5-[(1E)-3-hydroxy-4-phenylbut-1-enyl]-1-{4-[(triisopropylsilyl)thio]butyl}-pyrrolidin-2-one (540721-69-5)

Guidance literature:

Multi-step reaction with 6 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

With sodium tetrahydroborate; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; In 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) → (5R)-5-[(1E)-3-hydroxy-4-phenylbut-1-enyl]-1-{4-[(triisopropylsilyl)thio]butyl}-pyrrolidin-2-one (540721-69-5)

Guidance literature:

Multi-step reaction with 3 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

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

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

upstream raw materials:

triisopropylsilanethiol

(5R)-1-(4-chlorobutyl)-5-[(1E)-3-hydroxy-4-phenylbut-1-enyl]-pyrrolidin-2-one

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

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

Downstream raw materials:

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

(5R)-5-[(1E)-3-hydroxy-4-phenylbut-1-enyl]-1-[4-(methylthio)butyl]pyrrolidin-2-one

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