(2R)-Formyl-1-piperidinecarboxylic Acid Phenylmethyl Ester

Base Information

• Chemical Name: (2R)-Formyl-1-piperidinecarboxylic Acid Phenylmethyl Ester
• CAS No.: 1068012-41-8
• Molecular Formula: C14H17NO3
• Molecular Weight: 247.28968
• Mol file: 1068012-41-8.mol

Synonyms:(R)-N-Benzyloxycarbonyl-2-piperidinecarboxaldehyde;

Chemical Property of (2R)-Formyl-1-piperidinecarboxylic Acid Phenylmethyl Ester

Chemical Property:

• Boiling Point: 384.5±42.0 °C(Predicted)
• PKA: -3.02±0.40(Predicted)
• PSA: 46.61000
• Density: 1 +-.0.06 g/cm3(Predicted)
• LogP: 2.31450
• Solubility.: Dichloromethane, Ethyl Acetate

Purity/Quality:

97% ^*data from raw suppliers

(R)-N-Benzyloxycarbonyl-2-piperidinecarboxaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2R)-Formyl-1-piperidinecarboxylic Acid Phenylmethyl Ester

There total 14 articles about (2R)-Formyl-1-piperidinecarboxylic Acid Phenylmethyl Ester 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: 19.0%

benzyl (R)-2-([1,3]dithian-2-yl)piperidine-1-carboxylate (1067639-92-2) → (R)-N-(benzyloxycarbonyl)-2-formylpiperidine (1068012-41-8)

Guidance literature:

benzyl (R)-2-([1,3]dithian-2-yl)piperidine-1-carboxylate; With bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; methanol; at 20 ℃; for 0.25h;

With toluene-4-sulfonic acid; In 1,3-dioxane; water; at 50 ℃; for 3h; enantioselective reaction;

DOI:10.1055/s-2008-1067176

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (R)-N-(benzyloxycarbonyl)-2-formylpiperidine (1068012-41-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / 5percent aq. NaOH / 1 h / Ambient temperature

2: Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

3: DBU / toluene / 1 h / 100 °C

4: 1.) O₃, 2.) Me₂S / 1.) MeOH, -78 deg C, 2.) -78 deg C to room temp.

With sodium hydroxide; dimethylsulfide; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In dichloromethane; toluene;

DOI:10.1021/jo00124a025

Reference yield:

benzyl (R)-2-(hydroxymethyl)piperidine-1-carboxylate (154499-13-5) → (R)-N-(benzyloxycarbonyl)-2-formylpiperidine (1068012-41-8)

Guidance literature:

With sulfur trioxide pyridine complex; In dimethyl sulfoxide; for 0.5h; 0 deg C to room temp.;

DOI:10.1016/S0040-4039(00)78520-0

upstream raw materials:

benzyl (R)-2-(hydroxymethyl)piperidine-1-carboxylate

(2R)-N-(Carbobenzyloxy)-2-<2(E)-(3,4-dimethoxyphenyl)ethenyl>piperidine

benzyl chloroformate

(S)-2-<(Benzyloxy)methyl>-N-glutarimidopyrrolidine

Downstream raw materials:

(R)-2-((E)-2-Ethoxycarbonyl-vinyl)-piperidine-1-carboxylic acid benzyl ester

C₁₇H₂₃NO₆

C₁₇H₂₃NO₆

(R)-2-((1R,2S)-2-Ethoxycarbonyl-1,2-dihydroxy-ethyl)-piperidine-1-carboxylic acid benzyl ester

Refernces

• 1、 Gehring, Timo,Podlech, Joachim,Rothenberger, Alexander. "Intramolecular Michael-type additions to vinyl bissulfoxides: Enantioselective synthesis of chiral aldehydes". experimental part. p. 2476 - 2487. Retrieved 2009/04/07.
• 2、 Gurjar,Ghosh, Lakshmi,Syamala,Jayasree. "Stereoselective synthesis of (+)-and (-)-lentiginosine". . p. 8871 - 8872. Retrieved 2007/10/02.