N-Boc-piperidine-2-methanol Chemical Properties

Melting point:

74-78 °C

Boiling point:

308.0±15.0 °C(Predicted)

Density 

1.059±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

soluble in Methanol

pka

15.08±0.10(Predicted)

form 

Crystalline Powder

color 

White

InChI

InChI=1S/C11H21NO3/c1-11(2,3)15-10(14)12-7-5-4-6-9(12)8-13/h9,13H,4-8H2,1-3H3

InChIKey

PZTAGFCBNDBBFZ-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCCCC1CO

CAS DataBase Reference

157634-00-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

T

Risk Statements 

25-36/37/38

Safety Statements 

26-45

RIDADR 

UN 2811

WGK Germany 

3

HazardClass 

IRRITANT

HazardClass 

6.1

HS Code 

29333990

N-Boc-piperidine-2-methanol Usage And Synthesis

Chemical Properties

Solid

Uses

Reactant for:

• Julia coupling for synthesis of corydendramine A
• Cyclization-functionalization of nitrogen-containing dienes

• Heterocyclic compounds
• Anthranilamide inhibitors of factor Xa
• Human GnRH receptor antagonists
• Sphingosine-1-phosphate receptor agonists

Synthesis

The general procedure for the synthesis of 1-Boc-2-piperidinemethanol from di-tert-butyl dicarbonate and 2-piperidinemethanol is as follows: 1. 2-Piperidinemethanol (3.0 g, 25.60 mmol) was dissolved in dichloromethane (DCM, 100 mL) under stirring. 2. triethylamine (14.5 mL, 91.08 mmol) was added to the above solution in batches, followed by di-tert-butyl dicarbonate (7.2 g, 31.0 mmol). 3. The reaction mixture was stirred at room temperature for 16 hours. 4. Upon completion of the reaction, water (70 mL) was added for stratification to separate the organic layer. 5. The organic layer was washed with water (2 x 50 mL) and then dried with anhydrous sodium sulfate (Na2SO4). 6. The dried organic layer was filtered and concentrated under vacuum to give 1-Boc-2-piperidinemethanol (6.0 g, quantitatively) as a light brown oil, which can be used without further purification. The nuclear magnetic resonance hydrogen spectrum (1H NMR, CDCl3) data were as follows: δ 4.42-4.22 (1H, m), 4.05-3.91 (1H, m), 3.89-3.77 (1H, m), 3.71-3.53 (1H, m), 2.97-2.81 (1H, m), 2.32-2.08 (1H, m), 1.90 (1H, s ), 1.77-1.57 (3H, m), 1.54 (1H, s), 1.52-1.38 (10H, m).

References

[1] Patent: WO2007/141504, 2007, A1. Location in patent: Page/Page column 57
[2] Organic Letters, 1999, vol. 1, # 4, p. 667 - 670
[3] Journal of Organic Chemistry, 1996, vol. 61, # 17, p. 6040 - 6043
[4] Tetrahedron Asymmetry, 1998, vol. 9, # 11, p. 1951 - 1965
[5] Tetrahedron Letters, 2015, vol. 56, # 46, p. 6478 - 6483

N-Boc-piperidine-2-methanol(157634-00-9)Related Product Information

• Isobutyl chloroformate
• Butyl acetate
• Diisobutyl phthalate
• tert-Butyl peroxyacetate
• Butylparaben
• Diethylene glycol monobutyl ether
• 2-Butoxyethanol
• Methanol
• tert-Butanol
• RESMETHRIN
• tert-Butyl peroxybenzoate
• Buprofezin
• Cyhalofop-butyl
• 2,2,6,6-Tetramethyl-4-piperidinol
• Butyl benzoate
• N-Boc-piperidine-3-methanol
• Butyl acrylate
• 1-TERT-BUTYL 2-METHYL PIPERIDINE-1,2-DICARBOXYLATE