(3S,4S,1'S)-1-(1'-phenylethyl)-3-methyl-4-triisopropylsilyloxymethylpyrrolidin-2-one

Base Information

• Chemical Name: (3S,4S,1'S)-1-(1'-phenylethyl)-3-methyl-4-triisopropylsilyloxymethylpyrrolidin-2-one
• CAS No.: 1580503-64-5
• Molecular Formula: C₂₃H₃₉NO₂Si
• Molecular Weight: 389.654
• Mol file: 1580503-64-5.mol

Synonyms:(3S,4S,1'S)-1-(1'-phenylethyl)-3-methyl-4-triisopropylsilyloxymethylpyrrolidin-2-one

Chemical Property of (3S,4S,1'S)-1-(1'-phenylethyl)-3-methyl-4-triisopropylsilyloxymethylpyrrolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S,1'S)-1-(1'-phenylethyl)-3-methyl-4-triisopropylsilyloxymethylpyrrolidin-2-one

There total 2 articles about (3S,4S,1'S)-1-(1'-phenylethyl)-3-methyl-4-triisopropylsilyloxymethylpyrrolidin-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: 71.0%

(S)-1-((S)-1-phenylethyl)-4-(((triisopropylsilyl)oxy)methyl)pyrrolidin-2-one (1580503-61-2) + methyl iodide (74-88-4) → (3S,4S,1'S)-1-(1'-phenylethyl)-3-methyl-4-triisopropylsilyloxymethylpyrrolidin-2-one (1580503-64-5)

Guidance literature:

(S)-1-((S)-1-phenylethyl)-4-(((triisopropylsilyl)oxy)methyl)pyrrolidin-2-one; With n-butyllithium; In tetrahydrofuran; hexane; at -15 ℃; for 0.25h; Inert atmosphere;

methyl iodide; In tetrahydrofuran; hexane; at -15 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1007/s00726-014-1671-9

Reference yield:

(4S,1'S)-4-hydroxymethyl-1-(1'-phenylethyl)pyrrolidin-2-one (188641-35-2) → (3S,4S,1'S)-1-(1'-phenylethyl)-3-methyl-4-triisopropylsilyloxymethylpyrrolidin-2-one (1580503-64-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1H-imidazole / dichloromethane / 8 h / 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -15 °C / Inert atmosphere

2.2: 0.17 h / -15 °C / Inert atmosphere

With 1H-imidazole; n-butyllithium; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1007/s00726-014-1671-9

Reference yield: 46.0%

(3S,4S,1'S)-1-(1'-phenylethyl)-3-methyl-4-triisopropylsilyloxymethylpyrrolidin-2-one (1580503-64-5) + methyl chloroformate (79-22-1) → (3S,4S,1'S)-1-(1'-phenylethyl)-3-methyl-3-methoxycarbonyl-4-triisopropylsilyloxymethylpyrrolidin-2-one (1580503-67-8)

Guidance literature:

(3S,4S,1'S)-1-(1'-phenylethyl)-3-methyl-4-triisopropylsilyloxymethylpyrrolidin-2-one; With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; In tetrahydrofuran; hexane; at -15 ℃; for 0.25h; Inert atmosphere;

methyl chloroformate; In tetrahydrofuran; hexane; at -15 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1007/s00726-014-1671-9

upstream raw materials:

(4S,1'S)-4-hydroxymethyl-1-(1'-phenylethyl)pyrrolidin-2-one

(S)-1-((S)-1-phenylethyl)-4-(((triisopropylsilyl)oxy)methyl)pyrrolidin-2-one

methyl iodide

Downstream raw materials:

(3S,4S)-3-methyl-2-oxo-1-((S)-1-phenylethyl)-4-(((triisopropylsilyl)oxy)methyl)pyrrolidine-3-carboxylic acid

(3S,4S,1'S)-1-(1'-phenylethyl)-3-methyl-3-methoxycarbonyl-4-triisopropylsilyloxymethylpyrrolidin-2-one