4-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-PIPERIDINE-1,4-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER Chemical Properties

Melting point:

80-82 °C

Boiling point:

569.36°C (rough estimate)

Density 

1.2464 (rough estimate)

refractive index 

1.5300 (estimate)

storage temp. 

Inert atmosphere,2-8°C

pka

3.80±0.20(Predicted)

Appearance

White to off-white Solid

CAS DataBase Reference

183673-66-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

10

HS Code 

29225090

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

4-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-PIPERIDINE-1,4-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER Usage And Synthesis

Chemical Properties

N-Boc-amino-(4-N-Fmoc-piperidinyl)carboxylic Acid is white to cream crystalline powder or chunks

Uses

N-Boc-amino-(4-N-Fmoc-piperidinyl)carboxylic acid is used in the preparation of synthetic peptide amides as kappa opioid receptor agonists for treatment of pain, pruritis and inflammation associated w ith a variety of diseases.

Uses

Cyclic ?,?-disubstituted amino acid for the preparation of water-soluble highly helical peptides.

Synthesis

The general procedure for the synthesis of 4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid from methyl chloroformate-9-fluorenylmethyl and 4-amino-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid was as follows: 4-amino-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (5 g, 20.5 mmol) was dissolved in THF (300 mL), an aqueous solution of Na2CO3 (6.45 g, 61.5 mmol, 3.0 eq.) was added (64.5 mL) and cooled to 0 °C. A THF solution (30 mL) of methyl 9-fluorenyl chloroformate (5.3 g, 30.7 mmol, 1.5 eq.) was added slowly and dropwise. The reaction mixture was gradually warmed to 25 °C and stirring was continued for 12 hours. After completion of the reaction, the reaction solution was carefully acidified with 1 M HCl and the crude product was extracted three times with EtOAc. The organic layers were combined, dried with Na2SO4, concentrated and purified by combiflash column chromatography (eluent: 0 to 10% MeOH/DCM) to afford the target product 4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-1-(tert-butyloxycarbonyl)piperidine-4-carboxylic acid (4.02 g, 42% yield). The product was confirmed by 1H NMR, 13C NMR and HRMS characterization.

References

[1] Organic Syntheses, 2005, vol. 81, p. 213 - 224
[2] Patent: WO2015/184349, 2015, A2. Location in patent: Paragraph 0225-0226

4-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-PIPERIDINE-1,4-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER(183673-66-7)Related Product Information

• N-BOC-ISONIPECOTIC ACID
• 4-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-PIPERIDINE-1,4-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER
• 1-Boc-4-Methylaminopiperidine
• FMOC-D-DAB(FMOC)-OH
• 1-Amino-1-cyclohexanecarboxylic acid
• FMOC-DAB(BOC)-OH
• 1-tert-Butoxycarbonyl-4-piperidinecarboxaldehyde
• tert-Butyl N-(3-aminopropyl)-N-methylcarbamate
• N-Boc-4-piperidinemethanol
• Ethyl 4-hydroxypiperidine-1-carboxylate
• 4-Amino-1-Boc-piperidine
• 1-Boc-piperidine
• 1-BOC-4-METHYLPIPERIDINE
• Isopropyl 4-aminopiperidine-1-carboxylate
• FMOC-D-DAB-OH
• FMOC-DAB-OH HCL
• Propamocarb
• Fmoc-Aib-OH