(R)-3-(Boc-Amino)piperidine Chemical Properties

Melting point:

121.0 to 125.0 °C

Boiling point:

304.8±31.0 °C(Predicted)

Density 

1.02±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Soluble in methanol and ethanol.

pka

12.37±0.20(Predicted)

form 

Solid

color 

White to Off-White

optical activity

[α]22/D +3.2°, c = 0.5 in DMF

BRN 

10662518

InChI

InChI=1S/C10H20N2O2/c1-10(2,3)14-9(13)12-8-5-4-6-11-7-8/h8,11H,4-7H2,1-3H3,(H,12,13)/t8-/m1/s1

InChIKey

WUOQXNWMYLFAHT-MRVPVSSYSA-N

SMILES

C(OC(C)(C)C)(=O)N[C@@H]1CCCNC1

CAS DataBase Reference

309956-78-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,N

Risk Statements 

37/38-41-50

Safety Statements 

26-39-61-29-36

RIDADR 

3077

WGK Germany 

2

HazardClass 

9

PackingGroup 

Ⅲ

HS Code 

29333990

(R)-3-(Boc-Amino)piperidine Usage And Synthesis

Solubility in organics

Soluble in methanol and ethanol.

Uses

(R)-3-(Boc-amino)piperidine is Boc protected (R)-3-Aminopiperidine (A627920, Dihydrochloride salt) which has been used as a reactant for the preparation of dipeptidyl peptidase IV inhibitors derived from Alogliptin.

storage

Stable under recommended storage conditions. Incompatible with oxidizing agents.

Chemical Properties

White powder

Uses

(R)-3-(Boc-amino)piperidine is used as an organic chemical synthesis intermediate.

Synthesis

General procedure for the synthesis of (R)-3-Boc-aminopiperidine from benzyl (R)-3-((tert-butoxycarbonyl)amino)piperidine-1-carboxylate: 46.8 g of benzyl (R)-3-((tert-butoxycarbonyl)amino)piperidine-1-carboxylate (Compound IV), 2.3 g of 10% wet palladium-carbon (50% water) and 320 mL of methanol were added to an autoclave. The reaction system was replaced with nitrogen 3 to 4 times and the reaction temperature was raised to 35 to 40 °C under hydrogen pressure of 0.3 to 0.4 MPa and maintained for 2 hours. The progress of the reaction was monitored by HPLC until complete conversion of the feedstock. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated to be free of fractions. To the concentrate, 23 mL of dichloromethane and 46 mL of petroleum ether were added and the temperature was raised to 35 to 40 °C. At this temperature, 325 mL of petroleum ether was slowly added and held for 1 hour. The reaction mixture was then slowly cooled to -5~0°C and the solid product was collected by filtration. The solid was dried at 40~45°C to give 26.7 g of white solid (R)-3-Boc-aminopiperidine in 95.4% yield.

References

[1] Patent: CN105130879, 2018, B. Location in patent: Paragraph 0064; 0065; 0066; 0067; 0068; 0069; 0070
[2] Patent: WO2004/33455, 2004, A2. Location in patent: Page 27
[3] Patent: US2003/105077, 2003, A1

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