(2R,3S,4S)-1-Benzyl-2-[tert-butyl(dimethyl)silyloxymethyl]-3-(iodomethyl)-4-isopropenylpyrrolidine

Base Information

• Chemical Name: (2R,3S,4S)-1-Benzyl-2-[tert-butyl(dimethyl)silyloxymethyl]-3-(iodomethyl)-4-isopropenylpyrrolidine
• CAS No.: 313995-43-6
• Molecular Formula: C₂₂H₃₆INOSi
• Molecular Weight: 485.524
• Mol file: 313995-43-6.mol

Synonyms:(2R,3S,4S)-1-Benzyl-2-[tert-butyl(dimethyl)silyloxymethyl]-3-(iodomethyl)-4-isopropenylpyrrolidine

Chemical Property of (2R,3S,4S)-1-Benzyl-2-[tert-butyl(dimethyl)silyloxymethyl]-3-(iodomethyl)-4-isopropenylpyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S)-1-Benzyl-2-[tert-butyl(dimethyl)silyloxymethyl]-3-(iodomethyl)-4-isopropenylpyrrolidine

There total 8 articles about (2R,3S,4S)-1-Benzyl-2-[tert-butyl(dimethyl)silyloxymethyl]-3-(iodomethyl)-4-isopropenylpyrrolidine 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: 70.0%

N-Benzyl-N-[(1R)-1-(tert-butyl(dimethyl)siloxymethyl)prop-2-enyl]-N-[(2Z)-3-methyl-4-phenoxybut-2-enyl]amine (313995-42-5) → (2R,3S,4S)-1-Benzyl-2-[tert-butyl(dimethyl)silyloxymethyl]-3-(iodomethyl)-4-isopropenylpyrrolidine (313995-43-6)

Guidance literature:

N-Benzyl-N-[(1R)-1-(tert-butyl(dimethyl)siloxymethyl)prop-2-enyl]-N-[(2Z)-3-methyl-4-phenoxybut-2-enyl]amine; With titanium(IV) isopropylate; isopropylmagnesium chloride; In diethyl ether; at -50 - 20 ℃; for 1.16667h;

With iodine; In diethyl ether; at 0 ℃; for 0.5h; Further stages.;

DOI:10.1039/b005853j

Reference yield:

benzaldehyde (100-52-7) → (2R,3S,4S)-1-Benzyl-2-[tert-butyl(dimethyl)silyloxymethyl]-3-(iodomethyl)-4-isopropenylpyrrolidine (313995-43-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: Et₃N; Na₂SO₄ / CH₂Cl₂ / Heating

2.1: NaBH₄ / methanol / 1 h / 20 °C

3.1: 900 mg / imidazole / dimethylformamide

4.1: 86 percent / K₂CO₃; NaI / acetonitrile / Heating

5.1: Ti(O-iPr)4; iPr₂MgCl / diethyl ether / 1.17 h / -50 - 20 °C

5.2: 70 percent / I₂ / diethyl ether / 0.5 h / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; sodium tetrahydroborate; isopropylmagnesium chloride; potassium carbonate; sodium sulfate; triethylamine; sodium iodide; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.1: Condensation / 2.1: Reduction / 3.1: Etherification / 4.1: Alkylation / 5.1: Cyclization / 5.2: Iodination;

DOI:10.1039/b005853j

Reference yield:

{[(2Z)-4-Chloro-2-methylbut-2-enyl]oxy}benzene (221662-33-5) → (2R,3S,4S)-1-Benzyl-2-[tert-butyl(dimethyl)silyloxymethyl]-3-(iodomethyl)-4-isopropenylpyrrolidine (313995-43-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 86 percent / K₂CO₃; NaI / acetonitrile / Heating

2.1: Ti(O-iPr)4; iPr₂MgCl / diethyl ether / 1.17 h / -50 - 20 °C

2.2: 70 percent / I₂ / diethyl ether / 0.5 h / 0 °C

With titanium(IV) isopropylate; isopropylmagnesium chloride; potassium carbonate; sodium iodide; In diethyl ether; acetonitrile; 1.1: Alkylation / 2.1: Cyclization / 2.2: Iodination;

DOI:10.1039/b005853j

upstream raw materials:

N-Benzyl-N-[(1R)-1-(tert-butyl(dimethyl)siloxymethyl)prop-2-enyl]-N-[(2Z)-3-methyl-4-phenoxybut-2-enyl]amine

benzaldehyde

{[(2Z)-4-Chloro-2-methylbut-2-enyl]oxy}benzene

Methyl (2Z)-3-methyl-4-phenoxybut-2-enoate