(S)-3-Amino-1-N-Boc-piperidine Chemical Properties

alpha 

-28.5 º (c=1, DMF)

Boiling point:

277.3±33.0 °C(Predicted)

Density 

1.02

refractive index 

1.4690-1.4730

Flash point:

122℃

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

Soluble in dimethylsulfoxide.

pka

10.35±0.20(Predicted)

form 

Gum or Semi-Solid

color 

Colorless to yellow

optical activity

[α]/D +32.0±3°, c = 1 in DMF

Sensitive 

Air Sensitive

InChI

InChI=1S/C10H20N2O2/c1-10(2,3)14-9(13)12-6-4-5-8(11)7-12/h8H,4-7,11H2,1-3H3/t8-/m0/s1

InChIKey

AKQXKEBCONUWCL-QMMMGPOBSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCC[C@H](N)C1

CAS DataBase Reference

625471-18-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26

RIDADR 

2735

WGK Germany 

3

F 

10-34

HazardClass 

8

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich

(S)-3-Amino-1-N-Boc-piperidine Usage And Synthesis

Chemical Properties

Light yellow liquid

Uses

(S)-(+)-3-Amino-1-Boc-piperidine is used to prepare selective noncovalent inhibitors of the bacterial cysteine protease IdeS. The product obtained by the reductive elimination reaction with ethylglyoxalte is used as a reference compound, which is used to determine the absolute configuration of the two enantiomers.

Synthesis

General procedure for the synthesis of (S)-1-Boc-3-aminopiperidine from the compound (CAS:1271240-70-0): the azido derivative 42a (6.77 g, 29.9 mmol) was mixed with Pd/C catalyst (150 mg) in ethanol (200 mL) and subjected to a hydrogenation reaction at atmospheric pressure overnight. Upon completion of the reaction, the catalyst was removed by diatomaceous earth filtration followed by evaporation of the solvent. The product 43a was obtained as a colorless liquid in 90% yield (5.39 g, 26.9 mmol) without further purification. The 1H NMR, 13C NMR and IR spectral data of the product were in agreement with those reported in the literature30 . High-resolution mass spectrometry (HRMS, ESI) analysis showed a calculated and measured value of 201.1598 for C10H21O2N2 ([M + H]+); the specific spin [α]D20 was +26.0 (c 0.308, EtOH).

References

[1] Tetrahedron, 2011, vol. 67, # 7, p. 1485 - 1500
[2] Patent: WO2005/305, 2005, A1. Location in patent: Page 60
[3] Patent: WO2005/20976, 2005, A2. Location in patent: Page/Page column 239
[4] Patent: WO2005/60949, 2005, A2. Location in patent: Page/Page column 238

(S)-3-Amino-1-N-Boc-piperidine(625471-18-3)Related Product Information

• 4-AMINO-1-BOC-PIPERIDINE HYDROCHLORIDE
• N-BOC-3-Aminopiperidine
• DL-3-AMINO-1-N-BOC-PIPERIDINE
• (S)-3-Amino-1-N-Boc-piperidine
• (S)-3-AMINO-1-(TERT-BUTOXYCARBONYL)PIPERIDINE-3-CARBOXYLIC ACID
• 4-AMINO-1-N-BOC-PIPERIDINE
• (R)-3-AMINO-1-N-BOC-PIPERIDINE,(R)-3-Amino-1-N-Boc-Piperidine (R)-1-Boc-3-Aminopiperidine,(R)-3-AMINO-1-BOC-PIPERIDINE HYDROCHLORIDE
• 3-AMINOPIPERIDINE
• (S)-3-Aminopiperidine
• (S)-1-Boc-3-(Cbz-amino)-piperidine
• (S)-tert-Butyl 3-(methylsulfonamido)piperidine-1-carboxylate
• (1S,4S)-2-BOC-2,5-DIAZABICYCLO[2.2.2]OCTANE HYDROCHLORIDE
• (S)-1-BOC-3-N-(PYRIDIN-4-YLMETHYL)-AMINO-PIPERIDINE
• R-3-Dimethylamino-N-Boc-piperidine
• (1S,4S)-2-BOC-2,5-DIAZABICYCLO(2.2.2)OCTANE
• 1-N-Boc-3-(S)-Methylamino-piperidine
• 3-N-CBZ-AMINO-3-(3'-BOC)PIPERIDINE-PROPIONIC ACID
• S-3-(Carbamylamino)-N-Boc-piperidine