(2S)-2-[[[(1,1-DIMETHYLETHYL)DIPHENYLSILYL]OXY]METHYL]-5-OXO-1-PYRROLIDINE

Base Information

• Chemical Name: (2S)-2-[[[(1,1-DIMETHYLETHYL)DIPHENYLSILYL]OXY]METHYL]-5-OXO-1-PYRROLIDINE
• CAS No.: 132974-83-5
• Molecular Formula: C21 H27 NO2 Si
• Molecular Weight: 353.536
• Mol file: 132974-83-5.mol

Synonyms:(S)-5-(((tert-butydiphenylsilyl)oxy)methyl)pyrrolidin-2-one;

Chemical Property of (2S)-2-[[[(1,1-DIMETHYLETHYL)DIPHENYLSILYL]OXY]METHYL]-5-OXO-1-PYRROLIDINE

Chemical Property:

• Melting Point: 81-83 °C(Solv: hexane (110-54-3))
• Boiling Point: 467.1±27.0 °C(Predicted)
• PKA: 15.79±0.40(Predicted)
• PSA: 41.82000
• Density: 1.08±0.1 g/cm3(Predicted)
• LogP: 3.11750

Purity/Quality:

98.5% ^*data from raw suppliers

(2S)-2-[[[(1,1-DIMETHYL ETHYL)DIPHENYLSILYL]OXY]METHYL]-5-OXO-1-PYRROLIDINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2S)-2-[[[(1,1-DIMETHYLETHYL)DIPHENYLSILYL]OXY]METHYL]-5-OXO-1-PYRROLIDINE

There total 6 articles about (2S)-2-[[[(1,1-DIMETHYLETHYL)DIPHENYLSILYL]OXY]METHYL]-5-OXO-1-PYRROLIDINE 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: 100.0%

tert-butylchlorodiphenylsilane (58479-61-1) + (S)-Pyroglutaminol (17342-08-4) → (5S)-5-[[(tert-butyldiphenylsilyl)oxy]methyl]pyrrolidin-2-one (132974-83-5)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1016/S0040-4020(03)00377-6

Reference yield: 95.0%

(S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-oxopyrrolidine-1-carboxylate (138629-30-8,138871-56-4) → (5S)-5-[[(tert-butyldiphenylsilyl)oxy]methyl]pyrrolidin-2-one (132974-83-5)

Guidance literature:

With silica gel; In dichloromethane; for 0.0166667h; Irradiation;

DOI:10.1055/s-1998-1604

Reference yield:

methyl (S)-pyroglutamate (4931-66-2) → (5S)-5-[[(tert-butyldiphenylsilyl)oxy]methyl]pyrrolidin-2-one (132974-83-5)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₄ / methanol; tetrahydrofuran / 1 h

2: 66.0 g / imidazole / dimethylformamide / 20 h / 3 °C

With 1H-imidazole; sodium tetrahydroborate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1002/chem.200400181

upstream raw materials:

tert-butylchlorodiphenylsilane

(S)-Pyroglutaminol

(S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-oxopyrrolidine-1-carboxylate

methyl (S)-pyroglutamate

Downstream raw materials:

7-hydroxymethyl-1-(4-methoxy-benzylamino)-3-methyl-4a,5,6,7-tetrahydro-pyrrolo[1,2-c]pyrimidine-4-carboxylic acid methyl ester

7-(tert-butyl-diphenyl-silanyloxymethyl)-1-(4-methoxy-benzylamino)-3-methyl-4a,5,6,7-tetrahydro-pyrrolo[1,2-c]pyrimidine-4-carboxylic acid methyl ester

(4R,5S)-1-tert-butyloxycarbonyl-5-((tert-butyldiphenylsilyl)oxymethyl)-4-vinylpyrrolidin-2-one

(S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-oxo-3-phenylselanyl-pyrrolidine-1-carboxylic acid tert-butyl ester