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

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CAS:309956-78-3
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(R)-3-(Boc-Amino)piperidine Basic information
Solubility in organics Uses storage
Product Name:(R)-3-(Boc-Amino)piperidine
Synonyms:CARBAMIC ACID, (3R)-3-PIPERIDINYL-, 1,1-DIMETHYLETHYL ESTER;(R)-TERT-BUTYL-PIPERIDINE-3-YICARBAMATE;(R)-PIPERIDIN-3-YL-CARBAMIC ACID TERT-BUTYL ESTER;(R)-3-AMINO-N-TBOC-PIPERIDINE;tert-Butyl [(3R)-piperidin-3-yl]carbamate, (3R)-3-[(tert-Butoxycarbonyl)amino]piperidine;Linagliptin interMediate B;Alogliptin Benzoate interMediate F;(R)-3-(Boc-amino)piperidine,97%
CAS:309956-78-3
MF:C10H20N2O2
MW:200.28
EINECS:685-989-2
Product Categories:Piperidine Series;N-BOC;pharmacetical;Piperidine;Piperidines;Intermediates;309956-78-3
Mol File:309956-78-3.mol
(R)-3-(Boc-Amino)piperidine Structure
(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.
pka12.37±0.20(Predicted)
form Solid
color White to Off-White
Optical Rotation[α]22/D +3.2°, c = 0.5 in DMF
BRN 10662518
InChIInChI=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
InChIKeyWUOQXNWMYLFAHT-MRVPVSSYSA-N
SMILESC(OC(C)(C)C)(=O)N[C@@H]1CCCNC1
CAS DataBase Reference309956-78-3(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 
HS Code 29333990
Storage Class11 - Combustible Solids
Hazard ClassificationsAquatic Acute 1
Eye Dam. 1
Skin Irrit. 2
STOT SE 3
MSDS Information
(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 PropertiesWhite powder
Uses(R)-3-(Boc-amino)piperidine is used as an organic chemical synthesis intermediate.
Synthesis
(R)-3-N-BOC-AMINO-1-CBZ-PIPERIDINE

485820-12-0

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

309956-78-3

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
(R)-3-(Boc-Amino)piperidine Preparation Products And Raw materials
Raw materials(R)-3-N-BOC-AMINO-1-CBZ-PIPERIDINE-->(R)-1-Benzyl-3-N-Boc-aminopiperidine-->Palladium-->Methanol-->Hydrogen-->Activated carbon-->Water
Preparation Products(R)-3-Amino-1-methyl-piperidine
Tag:(R)-3-(Boc-Amino)piperidine(309956-78-3) Related Product Information
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