(3S)-1-(4-methoxyphenyl)-[(1R)-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one

Base Information

• Chemical Name: (3S)-1-(4-methoxyphenyl)-[(1R)-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one
• CAS No.: 141805-92-7
• Molecular Formula: C₁₈H₂₉NO₃Si
• Molecular Weight: 335.519
• Mol file: 141805-92-7.mol

Synonyms:(3S)-1-(4-methoxyphenyl)-[(1R)-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one

Chemical Property of (3S)-1-(4-methoxyphenyl)-[(1R)-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S)-1-(4-methoxyphenyl)-[(1R)-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one

There total 10 articles about (3S)-1-(4-methoxyphenyl)-[(1R)-(tert-butyldimethylsilyloxy)ethyl]azetidin-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: 61.0%

1-bromo-4-methoxy-benzene (104-92-7) + (1'R,3S)-3-<1'-<(tert-butyldimethylsilyl)oxy>ethyl>azetidin-2-one (109323-90-2) → (3S)-1-(4-methoxyphenyl)-[(1R)-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one (141805-92-7)

Guidance literature:

With copper(l) iodide; potassium carbonate; N,N-dimethylethylenediamine; at 105 ℃; for 24h; Inert atmosphere;

DOI:10.1021/jm200723m

Reference yield:

(4R)-3-<(2S,3R)-3-Hydroxy-2-<(benzyloxy)methyl>butanoyl>-4-isopropyl-1,3-thiazolidine-2-thione (141805-87-0) → (3S)-1-(4-methoxyphenyl)-[(1R)-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one (141805-92-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / imidazole / CH₂Cl₂ / 0 °C

2: CH₂Cl₂ / Ambient temperature

3: 91 percent / H₂ / 10percent Pd/C (H₂O) / methanol; acetic acid / 2 h / 3040 Torr / Ambient temperature

4: Et₃N / tetrahydrofuran / 1) 0 deg C, 30 min., 2) r.t., 1 h

5: NaH / CH₂Cl₂; dimethylformamide / 1.5 h / Ambient temperature

With 1H-imidazole; hydrogen; sodium hydride; triethylamine; palladium on carbon; In tetrahydrofuran; methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/jo00041a033

Reference yield:

(2S,3R)-3-<(tert-Butyldimethylsilyl)oxy>-2-<(benzyloxy)methyl>-N-(4-methoxyphenyl)butylamide (141805-89-2) → (3S)-1-(4-methoxyphenyl)-[(1R)-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one (141805-92-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / H₂ / 10percent Pd/C (H₂O) / methanol; acetic acid / 2 h / 3040 Torr / Ambient temperature

2: Et₃N / tetrahydrofuran / 1) 0 deg C, 30 min., 2) r.t., 1 h

3: NaH / CH₂Cl₂; dimethylformamide / 1.5 h / Ambient temperature

With hydrogen; sodium hydride; triethylamine; palladium on carbon; In tetrahydrofuran; methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/jo00041a033

upstream raw materials:

(2S,3R)-3-<(tert-Butyldimethylsilyl)oxy>-2-<(methanesulfonyl)methyl>-N-(4-methoxyphenyl)butylamide

1,3,5-tris(4-methoxyphenyl)-1,3,5-triazinane

(R)-3-(tert-butyldimethylsiloxy)butanoyl chloride

3-(R)-t-butyldimethylsilyloxybutanoic acid

Downstream raw materials:

(3S)-1-(4-methoxyphenyl)-[(1R)-(4-phenylbutoxy)ethyl]azetidin-2-one

(3S)-1-(4-methoxyphenyl)-[(1R)-hydroxyethyl]azetidin-2-one