(S)-(+)-N-tert-butyloxycarbonyl-5-(triisopropylsilyloxymethyl)pyrrolid-3-en-2-one

Base Information

• Chemical Name: (S)-(+)-N-tert-butyloxycarbonyl-5-(triisopropylsilyloxymethyl)pyrrolid-3-en-2-one
• CAS No.: 222307-12-2
• Molecular Formula: C₁₉H₃₅NO₄Si
• Molecular Weight: 369.577
• Mol file: 222307-12-2.mol

Synonyms:(S)-(+)-N-tert-butyloxycarbonyl-5-(triisopropylsilyloxymethyl)pyrrolid-3-en-2-one

Chemical Property of (S)-(+)-N-tert-butyloxycarbonyl-5-(triisopropylsilyloxymethyl)pyrrolid-3-en-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-(+)-N-tert-butyloxycarbonyl-5-(triisopropylsilyloxymethyl)pyrrolid-3-en-2-one

There total 1 articles about (S)-(+)-N-tert-butyloxycarbonyl-5-(triisopropylsilyloxymethyl)pyrrolid-3-en-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:

(S)-Pyroglutaminol (17342-08-4) → (S)-(+)-N-tert-butyloxycarbonyl-5-(triisopropylsilyloxymethyl)pyrrolid-3-en-2-one (222307-12-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 66 percent / imidazole / dimethylformamide

2.1: 85 percent / 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂

3.1: LiHMDS / tetrahydrofuran / -78 °C

3.2: tetrahydrofuran / -78 °C

3.3: 59 percent / H₂O₂ / ethyl acetate / 0 °C

With 1H-imidazole; dmap; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2005.12.068

Reference yield: 91.0%

N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine (93102-05-7) + (S)-(+)-N-tert-butyloxycarbonyl-5-(triisopropylsilyloxymethyl)pyrrolid-3-en-2-one (222307-12-2) → C28H46N2O4Si (1210431-00-7)

Guidance literature:

N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine; (S)-(+)-N-tert-butyloxycarbonyl-5-(triisopropylsilyloxymethyl)pyrrolid-3-en-2-one; With trifluoroacetic acid; In dichloromethane; at 20 ℃;

With triethylamine; In dichloromethane;

Reference yield: 28.0%

(S)-(+)-N-tert-butyloxycarbonyl-5-(triisopropylsilyloxymethyl)pyrrolid-3-en-2-one (222307-12-2) + 1,3-bis(benzyl)-4-(hydroxypropenyl)-1,3-dihydro-imidazol-2-one (896140-74-2) → 1,3-dibenzyl-5-hydroxymethyl-2,6-dioxo-8-triisopropylsilanyloxymethyl-2,3,4,5,5a,6,8,8a-octahydro-1H-imidazo[4,5-e]isoindole-7-carboxylic acid tert-butyl ester

Guidance literature:

In o-xylene; at 140 ℃; for 24h;

DOI:10.1016/j.tet.2005.12.068

upstream raw materials:

(S)-Pyroglutaminol

Downstream raw materials:

C₂₈H₄₆N₂O₄Si