allyl 1-benzyl-3-oxo-4-piperidinecarboxylate

Base Information

• Chemical Name: allyl 1-benzyl-3-oxo-4-piperidinecarboxylate
• CAS No.: 217488-44-3
• Molecular Formula: C₁₆H₁₉NO₃
• Molecular Weight: 273.332
• Mol file: 217488-44-3.mol

Synonyms:allyl 1-benzyl-3-oxo-4-piperidinecarboxylate

Chemical Property of allyl 1-benzyl-3-oxo-4-piperidinecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 1-benzyl-3-oxo-4-piperidinecarboxylate

There total 1 articles about allyl 1-benzyl-3-oxo-4-piperidinecarboxylate 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: 62.0%

ethyl 1-benzyl-3-oxo-4-piperidinecarboxylate (39514-19-7) + sodium allyloxide (20907-32-8) → allyl 1-benzyl-3-oxo-4-piperidinecarboxylate (217488-44-3)

Guidance literature:

With allyl alcohol; for 10h; Heating;

DOI:10.1248/cpb.48.716

Reference yield: 99.0%

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one (76899-07-5,78963-47-0,78963-48-1,78963-60-7,80951-41-3,81275-02-7,85647-75-2,85954-95-6,92217-74-8,104527-11-9,76855-69-1) + allyl 1-benzyl-3-oxo-4-piperidinecarboxylate (217488-44-3) → (3S,4R)-4-[4-(allyloxycarbonyl)-1-benzyl-3-oxopiperidin-4-yl]-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone (277334-45-9)

Guidance literature:

allyl 1-benzyl-3-oxo-4-piperidinecarboxylate; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 0.5h;

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1248/cpb.48.716

Reference yield:

allyl 1-benzyl-3-oxo-4-piperidinecarboxylate (217488-44-3) → (3R,4S)-4-[(R)-1-benzyl-3-oxopiperidin-4-yl]-1-(tert-butyldimethylsilyl)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone (217488-46-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

1.2: 99 percent / tetrahydrofuran / 0.5 h / 0 °C

2.1: 2,6-lutidine / CH₂Cl₂ / 0.17 h / 0 °C

3.1: Pd(PPh₃)4; PPh₃; Et₃N / ethyl acetate; formic acid / 2.5 h / 0 °C

With 2,6-dimethylpyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; formic acid; dichloromethane; ethyl acetate; 1.1: Metallation / 2.1: Silylation / 3.1: Decarboxylation;

DOI:10.1248/cpb.48.716

upstream raw materials:

ethyl 1-benzyl-3-oxo-4-piperidinecarboxylate

sodium allyloxide

Downstream raw materials:

(3S,4R)-4-[4-(allyloxycarbonyl)-1-benzyl-3-oxopiperidin-4-yl]-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone

(3R,4S)-4-[(R)-1-benzyl-3-oxopiperidin-4-yl]-1-(tert-butyldimethylsilyl)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone

1-benzyl-4-{1-(tert-butyl-dimethyl-silanyl)-3-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-3-oxo-piperidine-4-carboxylic acid allyl ester