N-Boc-piperidine-3-methanol Chemical Properties

Melting point:

77-81 °C

Boiling point:

308.0±15.0 °C(Predicted)

Density 

1.059±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in methanol and dimethylformamide(DMF).

form 

powder to crystal

pka

14.93±0.10(Predicted)

color 

White to Almost white

InChI

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

InChIKey

OJCLHERKFHHUTB-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

116574-71-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333990

N-Boc-piperidine-3-methanol Usage And Synthesis

Chemical Properties

White solid

Uses

(+/-)-1-Boc-3-(hydroxymethyl)piperidine is used as a reactant for synthesis of Pim-1 inhibitors, Vasopressin1b receptor antagonists, CXCR4 antagonists as anti-HIV agents, Amide CCR5 antagonist, PSSRI-based inhibitors of S. aureus multidrug efflux pumps and Human GnRH receptor antagonists.

Uses

Reactant for synthesis of:

• Pim-1 inhibitors
• Vasopressin1b receptor antagonists
• CXCR4 antagonists as anti-HIV agents
• Amide CCR5 antagonist
• PSSRI-based inhibitors of S. aureus multidrug efflux pumps
• Human GnRH receptor antagonists

Synthesis

(1) Preparation of 3-(hydroxymethyl)-1-(tert-butoxycarbonyl)piperidine: To a solution of 3-hydroxymethylpiperidine (1.15 g, 10 mmol) in tetrahydrofuran (15 ml) was added triethylamine (2.8 ml, 20 mmol) at room temperature. Subsequently, a solution of di-tert-butyl dicarbonate (2.62 g, 10 mmol) in tetrahydrofuran (5 ml) was added slowly and dropwise with stirring. The reaction mixture was stirred continuously for 20 hours at room temperature. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was dissolved in ethyl acetate (50 ml), and the organic phase was washed sequentially with water and saturated saline, and then dried with anhydrous sodium sulfate. Finally, the solvent was removed by reduced pressure distillation to afford the target product tert-butyl 3-(hydroxymethyl)piperidine-1-carboxylate (2.15 g, 100% yield) as colorless crystals. The product was confirmed by 1H-NMR (CDCl3) and IR (KBr) characterization.1H-NMR (CDCl3) δ: 1.2-1.4 (2H, m), 1.46 (9H, s), 1.5-1.9 (4H, m), 2.8-3.3 (2H, m), 3.51 (2H, t, J = 6.10 Hz), 3.6-3.9 (2H, m) IR (KBr) cm-1: 3491, 1742, 1674, 1428, 1269, 1177, 1153, 858, 769.

References

[1] Patent: US6348468, 2002, B1. Location in patent: Page column 49
[2] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 4, p. 1084 - 1088
[3] Patent: US2004/67935, 2004, A1. Location in patent: Page/Page column 28
[4] Patent: US2002/65265, 2002, A1
[5] Patent: WO2004/72086, 2004, A2. Location in patent: Page 170

N-Boc-piperidine-3-methanol(116574-71-1)Related Product Information

• n-boc-piperidine-2-methanol,1-Boc-Piperidine-2-Methanol
• N-Boc-4-piperidinemethanol
• 1-TERT-BUTYL 2-METHYL PIPERIDINE-1,2-DICARBOXYLATE
• N-BOC-3-Aminopiperidine
• 1-BOC-3-PIPERIDINECARBOXALDEHYDE
• (+/-)-1-N-BOC-PIPERIDINE-2-CARBOXAMIDE
• 1-tert-Butoxycarbonyl-4-piperidinecarboxaldehyde
• N-BOC-piperidine-4-carboxylic acid
• N-Boc-2-piperidinecarboxylic acid
• Ethyl N-Boc-piperidine-4-carboxylate
• Ethyl 1-Boc-piperidine-2-carboxylate
• 1-Boc-3-hydroxypiperidine
• N-Boc-Piperidine-4-carboxylic acid methyl ester
• TERT-BUTYL 4-(AMINOCARBONYL)TETRAHYDROPYRIDINE-1(2H)-CARBOXYLATE
• 1-Boc-4-Methylaminopiperidine
• 1-N-BOC-PIPERIDINE-3-CARBOXAMIDE
• 1-Boc-3-piperidone
• N-(tert-Butoxycarbonyl)-4-piperidone