rac- (2E)-3-[(Ethoxycarbonyl)Methylene]-1-trityl-4-piperidinol

Base Information

• Chemical Name: rac- (2E)-3-[(Ethoxycarbonyl)Methylene]-1-trityl-4-piperidinol
• CAS No.: 239466-40-1
• Molecular Formula: C28H29NO3
• Molecular Weight: 427.543
• Mol file: 239466-40-1.mol

Synonyms:(E)-3-ethoxycarbonylmethylidene-4-hydroxy-1-triphenylmethylpiperidine;(E)-3-[(ethoxycarbonyl)methylidene]-1-(triphenylmethyl)piperidine-4-ol;Acetic acid,2-[4-hydroxy-1-(triphenylmethyl)-3-piperidinylidene]-,ethyl ester,(2E);ACE056;(E)-3-[(ethoxycarbonyl)methylidene]-1-(triphenylmethyl)piperidin-4-ol;

Chemical Property of rac- (2E)-3-[(Ethoxycarbonyl)Methylene]-1-trityl-4-piperidinol

Chemical Property:

• Boiling Point: 565.3±50.0 °C(Predicted)
• PKA: 13.74±0.20(Predicted)
• PSA: 49.77000
• Density: 1.209±0.06 g/cm3(Predicted)
• LogP: 4.47250
• Solubility.: Chloroform, Dichloromethane, Ether, Ethyl Acetate, Methanol

Purity/Quality:

96% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of rac- (2E)-3-[(Ethoxycarbonyl)Methylene]-1-trityl-4-piperidinol

There total 4 articles about rac- (2E)-3-[(Ethoxycarbonyl)Methylene]-1-trityl-4-piperidinol 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%

→ p-toluenesulfonate salt of 3-ethoxycarbonylmethylidene-4-hydroxypiperidine + ethyl (E)-2-(4-hydroxy-1-tritylpiperidin-3-ylidene)acetate (239466-40-1)

Guidance literature:

Reference yield: 57.9%

E-2-(4-carbonyl-1-tritylpiperidin-3-ylidene)ethyl acetate (239466-39-8) → ethyl (E)-2-(4-hydroxy-1-tritylpiperidin-3-ylidene)acetate (239466-40-1)

Guidance literature:

With methanol; sodium tetrahydroborate; In dichloromethane; at 20 ℃; for 1h; Cooling with ice;

Reference yield:

trityl chloride (76-83-5) → ethyl (E)-2-(4-hydroxy-1-tritylpiperidin-3-ylidene)acetate (239466-40-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / N,N-dimethyl-formamide / 5 h / 60 °C

2.1: pyrrolidine / toluene / 3 h / Reflux

2.2: 2 h / Reflux

3.1: sodium tetrahydroborate; methanol / dichloromethane / 1 h / 20 °C / Cooling with ice

With pyrrolidine; methanol; sodium tetrahydroborate; triethylamine; In dichloromethane; N,N-dimethyl-formamide; toluene;

upstream raw materials:

trityl chloride

1-triphenylmethyl-4-piperidone

E-2-(4-carbonyl-1-tritylpiperidin-3-ylidene)ethyl acetate

Downstream raw materials:

(E)-3-carboxymethylidene-4-hydroxy-1-triphenylmethylpiperidine

(E)-4-(t-butyldimethylsilyloxy)-3-[(ethoxycarbonyl)methylidene]-1-(triphenylmethyl)piperidine

(E)-3-[(ethoxycarbonyl)methylidene]-4-mesyloxy-1-(triphenylmethyl)piperidine

2-[(3E)-1-[(1S)-1-(2-chlorophenyl)-2-methoxy-2-oxoethyl]-4-mercaptopiperidine-3-ylidene]acetic acid