(R)-(+)-N-Boc-2-piperidinecarboxylic acid Chemical Properties

Melting point:

116-119 °C(lit.)

alpha 

68 º (c=1 in acetic acid)

Boiling point:

353.2±35.0 °C(Predicted)

Density 

1.164±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in 2ml dimethyl formamide 0.3gram.

form 

Crystalline Powder

pka

4.03±0.20(Predicted)

color 

White to brown

optical activity

[α]23/D 63.5±3°, c = 1 in acetic acid

BRN 

480023

InChIKey

JQAOHGMPAAWWQO-MRVPVSSYSA-N

CAS DataBase Reference

28697-17-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

(R)-(+)-N-Boc-2-piperidinecarboxylic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

It is also applied as catalytic agent and petrochemical additive. It is also an important organic intermediate used in agrochemicals, pharmaceuticals and dyestuff fields.

Uses

(R)-(+)-N-Boc-2-piperidinecarboxylic Acid is a useful intermediate for agrochemical, pharmaceuticals and dye industries.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

The general procedure for the synthesis of (R)-1-(tert-butoxycarbonyl)piperidine-2-carboxylic acid from di-tert-butyl dicarbonate and D-(+)-2-piperidinic acid was as follows: to a 1000 mL round-bottomed flask were added D-(+)-2-piperidinic acid (8.0 g, 0.062 mol), di-tert-butyl dicarbonate (14.8 g, 0.068 mol), sodium bicarbonate (26.04 g, 0.310 mol) and methanol (400 mL). The mixture was stirred and reacted at room temperature for 24 hours. Upon completion of the reaction, methanol was removed by distillation under reduced pressure. The residue was dissolved in water and subsequently washed three times with ether. The pH of the aqueous phase was adjusted to 2 with saturated potassium bisulfate solution and then extracted three times with dichloromethane. The organic phases were combined, washed three times with saturated saline, dried over anhydrous sodium sulfate and concentrated. The crude product was purified by silica gel column chromatography with the eluent being a mixed solvent of petroleum ether/ethyl acetate/acetic acid, resulting in 12.48 g of white solid product in 87.8% yield. The product was characterized by 1H-NMR (400 MHz, DMSO) and EI-MS: 1H-NMR δ 12.71 (1H, s), 4.61 (1H, d, J = 28.8 Hz), 3.82 (1H, d, J = 12 Hz), 2.93 (1H, m), 2.06 (1H, s), 1.62 (3H, m), 1.39 (11H, m); EI-MS m/z: 229.1 [M]+.

References

[1] Journal of Medicinal Chemistry, 1998, vol. 41, # 4, p. 591 - 601
[2] Journal of Medicinal Chemistry, 1992, vol. 35, # 9, p. 1550 - 1557
[3] ChemMedChem, 2013, vol. 8, # 4, p. 577 - 581
[4] Patent: EP2805947, 2014, A1. Location in patent: Paragraph 0074-0075
[5] Patent: US2015/126500, 2015, A1. Location in patent: Paragraph 0127; 0128

(R)-(+)-N-Boc-2-piperidinecarboxylic acid(28697-17-8)Related Product Information

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• Triacetonediamine
• Glycine
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• DROPERIDOL
• Folic acid
• Oxygen-fluorine acid
• Ethyl 2-(Chlorosulfonyl)acetate
• Levofloxacin carboxylic acid
• Citric acid
• Haloperidol
• DL-Pipecolinic acid
• DI-TERT-BUTYL ETHER
• Diphenoxylate
• D(+)-Pipecolinic acid
• N-Boc-2-piperidinecarboxylic acid
• (R)-(+)-N-Boc-2-piperidinecarboxylic acid
• phosphoric acid