N-Boc-Piperidine-4-carboxylic acid methyl ester Chemical Properties

Melting point:

33.0 to 37.0 °C

Boiling point:

307.4±35.0 °C(Predicted)

Density 

1.094±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

soluble in Methanol

form 

powder to lump

pka

-2.29±0.40(Predicted)

color 

White to Light yellow

InChI

InChI=1S/C12H21NO4/c1-12(2,3)17-11(15)13-7-5-9(6-8-13)10(14)16-4/h9H,5-8H2,1-4H3

InChIKey

PTZNCCIULVXFIJ-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCC(C(OC)=O)CC1

CAS DataBase Reference

124443-68-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

HazardClass 

IRRITANT

HS Code 

29333990

N-Boc-Piperidine-4-carboxylic acid methyl ester Usage And Synthesis

Chemical Properties

White solid

Uses

Methyl (1-BOC-piperidin-4-yl)carboxylate can be used as orexin type-2 receptor agonist.

Synthesis

General procedure for the synthesis of methyl 1-tert-butoxycarbonyl-4-piperidinecarboxylate from methanol and 1-Boc-4-piperidinecarboxylic acid: a hexane solution of trimethylmethylsilyl diazomethane (2.00 M, 52.9 mL, 106 mmol) was added slowly and dropwise at 0 °C to a 1-tert-butoxycarbonyl-piperidine-4-carboxylic acid (12.14 g, 52.95 mmol) acetonitrile ( 100 mL) suspension. Methanol (10 mL) was then added. The reaction mixture was allowed to stand at 0 °C for 30 min and then stirred at room temperature for 3 h. The reaction was carried out under reduced pressure. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography [hexane/ethyl acetate (4.5:1, v/v)] to afford 1-tert-butyl 4-methylpiperidine-1,4-dicarboxylate as a colorless oil (11.5 g, 90% yield). The structure of the product was confirmed by 1H NMR (400 MHz, d6-DMSO): δ 4.02 (dt, 2H, J = 3.5, 13.7 Hz), 3.69 (s, 3H), 2.82 (ddd, 2H, J = 3, 11.5, 14.5 Hz), 2.45 (tt, 1H, J = 3.9, 11.5 Hz), 1.90-1.84 ( m, 2H), 1.67-1.57 (m, 2H), 1.45 (s, 9H). Mass spectral analysis (ES) showed m/z 265.8 (MNa+); calculated value: 243.1 (M).

References

[1] Patent: WO2006/86609, 2006, A2. Location in patent: Page/Page column 160
[2] Tetrahedron Letters, 2004, vol. 45, # 12, p. 2663 - 2665
[3] Tetrahedron Letters, 2011, vol. 52, # 8, p. 849 - 852

N-Boc-Piperidine-4-carboxylic acid methyl ester(124443-68-1)Related Product Information

• Ethyl N-Boc-piperidine-4-carboxylate
• tert-Butyl acetate
• Tribenuron methyl
• Isonipecotic acid
• Methyl salicylate
• Methyl benzoate
• Methyl anthranilate
• Kresoxim-methyl
• tert-Butyl peroxyacetate
• Methyl carbamate
• Methyl acrylate
• tert-Butanol
• Methyl isonipecotate
• Methyl formate
• Methylparaben
• N-BOC-piperidine-4-carboxylic acid
• Thiophanate-methyl
• 1-TERT-BUTYL 2-METHYL PIPERIDINE-1,2-DICARBOXYLATE