L-1-Boc-Nipecotic 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 

solid

color 

White to off-white

optical activity

[α]22/D +57°, c = 1 in chloroform

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)/t8-/m0/s1

InChIKey

NXILIHONWRXHFA-QMMMGPOBSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCC[C@H](C(O)=O)C1

CAS DataBase Reference

88495-54-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,N

Risk Statements 

36/37/38-50

Safety Statements 

26-36-61

RIDADR 

UN 3077 9/PG 3

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

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

L-1-Boc-Nipecotic acid Usage And Synthesis

Chemical Properties

White powder

Uses

1-Boc-L-nipecotic acid is used as an organic chemical synthesis intermediate.

Synthesis

The general procedure for the synthesis of 1-BOC-piperidine-3-carboxylic acid from di-tert-butyl dicarbonate and 3-piperidinecarboxylic acid was as follows: 1. To a solution of piperidine-3-carboxylic acid (50.0 g, 387.5 mmol) in tert-butanol (464.0 mL) was slowly added 1N NaOH solution (464.0 mL) at 0 °C and stirred for 10 min. 2. Di-tert-butyl dicarbonate (Boc-anhydride, 143.6 g, 659.0 mmol) was then added. 3. The reaction mixture was stirred continuously at room temperature for 12 hours. 4. Upon completion of the reaction, the reaction mixture was concentrated under reduced pressure and then neutralized to neutrality with 1N HCl solution. 5. The precipitated solid product was collected by filtration and dried to give 1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid (1, 86.0 g, 97% yield) as a white solid. Product characterization data: 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

L-1-Boc-Nipecotic acid(88495-54-9)Related Product Information

• DROPERIDOL
• Di-tert-butyl dicarbonate
• Folic acid
• Nipecotic acid
• 2,2,6,6-Tetramethyl-4-piperidinol
• Ethyl 2-(Chlorosulfonyl)acetate
• Haloperidol
• PHENCYCLIDINE-D5 HYDROCHLORIDE
• Glycine
• 1,3-Piperidinedicarboxylic acid, 1-(1,1-dimethylethyl) 3-ethyl ester, (3S)- (9CI)
• (R)-3-AMINO-1-(TERT-BUTOXYCARBONYL)PIPERIDINE-3-CARBOXYLIC ACID
• Piperidine
• Diphenoxylate
• 1-Boc-3-piperidinecarboxylic acid
• N-Boc-nipecotic acid methyl ester
• N-BOC-DL-PIPECOLINIC ACID
• 4-AMINO-1-BOC-PIPERIDINE-4-CARBOXYLIC ACID
• 4-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-PIPERIDINE-1,4-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER