1-Boc-3-piperidinecarboxylic acid Chemical Properties

Melting point:

159-162 °C(lit.)

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

pka

4.49±0.20(Predicted)

form 

Crystalline Powder

color 

White

BRN 

5539297

InChI

InChI=1S/C11H19NO4/c1-11(2,3)16-10(15)12-6-4-5-8(7-12)9(13)14/h8H,4-7H2,1-3H3,(H,13,14)

InChIKey

NXILIHONWRXHFA-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCCC(C(O)=O)C1

CAS DataBase Reference

84358-12-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

1-Boc-3-piperidinecarboxylic acid Usage And Synthesis

Chemical Properties

White crystalline powder

Uses

peptide synthesis

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

The general procedure for the synthesis of 1-BOC-piperidine-3-carboxylic acid from di-tert-butyl dicarbonate and 3-piperidinecarboxylic acid is as follows:1. Dissolve piperidine-3-carboxylic acid (50.0 g, 387.5 mmol) in tert-butyl alcohol (464.0 mL) at 0 °C, slowly add 1N NaOH solution (464.0 mL), and stir for 10 min. 2. Add di-tert-butyl dicarbonate (Boc-anhydride, 143.6 g, 659.0 mmol) to the above solution. 3. Stir the reaction mixture for 12 hours at room temperature. 4. Di-tert-butyl carbonate (Boc-anhydride, 143.6 g, 659.0 mmol) was added to the above solution. 3. The reaction mixture was stirred at room temperature for 12 h. 4. Upon completion of the reaction, the reaction mixture was concentrated under reduced pressure, and then neutralized to pH neutral with 1N HCl solution. 5. The precipitated white solid was collected by filtration, and dried to give 1-BOC-piperidine-3-carboxylic acid (1 , 86.0 g, yield 97%). The product was characterized by 1H NMR (400 MHz, DMSO-d6), δ 1.38 (s, 9H), 1.47 (m, 1H), 1.59 (dt, J = 3.8 Hz, 1H), 1.87 (m, 1H), 2.28 (m, 1H), 2.77-2.84 (dt, J = 2.5,3.0 Hz, 1H), 3.0 (brs. 1H), 3.67 (d, J = 11.0 Hz, 1H), 3.87 (brs, 1H), 12.2 (s, 1H).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 8, p. 2118 - 2122
[2] Patent: WO2014/149164, 2014, A1. Location in patent: Paragraph 00604
[3] Journal of Medicinal Chemistry, 2004, vol. 47, # 7, p. 1719 - 1728
[4] Beilstein Journal of Organic Chemistry, 2013, vol. 9, p. 966 - 973
[5] European Journal of Organic Chemistry, 2005, # 4, p. 673 - 682

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