(S)-3-(Boc-amino)pyrrolidine Chemical Properties

Melting point:

50 °C

Boiling point:

112°C/0.25mm

Density 

1.04±0.1 g/cm3(Predicted)

refractive index 

-20 ° (C=1, EtOH)

storage temp. 

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

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

12.37±0.20(Predicted)

form 

Powder

color 

White to off-white

optical activity

[α]/D -21.5±2.0°, c = 1 in ethanol

Water Solubility 

Soluble in water.

Sensitive 

Air Sensitive

BRN 

5377813

InChI

InChI=1S/C9H18N2O2/c1-9(2,3)13-8(12)11-7-4-5-10-6-7/h7,10H,4-6H2,1-3H3,(H,11,12)/t7-/m0/s1

InChIKey

DQQJBEAXSOOCPG-ZETCQYMHSA-N

SMILES

C(OC(C)(C)C)(=O)N[C@H]1CCNC1

CAS DataBase Reference

122536-76-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,C

Risk Statements 

36/37/38

Safety Statements 

26

RIDADR 

3259

WGK Germany 

3

F 

10-23

HazardClass 

8

PackingGroup 

III

HS Code 

29339900

MSDS

• Language:English Provider:tert-Butyl-(S)-3-pyrrolidinylcarbamate
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

(S)-3-(Boc-amino)pyrrolidine Usage And Synthesis

Chemical Properties

White crystalline powder

Uses

(S)-3-(Boc-amino)pyrrolidine can be used as a building block to prepare:

• 2,4,6-trisubstitued pyrido[3,4-d]pyrimidine derivatives as potent inhibitors against EGFR tyrosine kinase.
• Aminopyrrolidine scaffolds for asymmetric Morita?Baylis-Hillman reaction.
• N-benzyl-3-sulfonamidopyrrolidines as potent bacterial cell division inhibitors.

Synthesis

1. In a 500 mL four-necked flask fitted with a stirrer, thermometer, Dimroth condenser and titration funnel, 17.6 g (0.1 mol, optical purity 99.5% ee) of (S)-3-amino-1-benzylpyrrolidine was added. Subsequently, 158.7 g of water and 0.2 g of cationic DS (produced by Sanyo Chemical Industries, Ltd.) were added and the pH of the mixture was adjusted to 11 ± 0.5 using 48% aqueous sodium hydroxide solution. 2. The mixture was stirred at 50 to 60 °C while 26.2 g (0.12 mol) of di-tert-butyl dicarbonate (DiBoc) was added dropwise for about 2 hours. During the dropwise addition, the pH of the reaction solution was maintained at 11 ± 0.5 using 48% aqueous sodium hydroxide. 3. After completion of the dropwise addition, stirring was continued for 1 hour, after which the reaction solution was cooled to room temperature and the precipitated crystals were separated by filtration. 4. The resulting crystals were dried under vacuum at 50 °C to afford 26.0 g of (S)-1 -benzyl-3-tert-butoxycarbonylaminopyrrolidine in 94.1% yield, 99.1% chemical purity and 99.5% optical purity ee. 5. Using the same apparatus as in Step 1 , 26.0 g (optical purity 99.5% ee) of (S)-1 -benzyl-3-tert-butoxycarbonylaminopyrrolidine, 120 g of water, and 2.6 g of 5% Pd/C (PE-type, 55.27% water content, manufactured by NE Chemcat Corp.) were added. The reaction was stirred at 40°C reaction temperature for 10 hours under hydrogen atmosphere. 6. After confirming the completion of the reaction by GC analysis, the Pd/C was removed by filtration and the filtrate was concentrated to 30 g using an evaporator. 7. The concentrated product was mixed with toluene and concentrated again to 20 g to remove water by azeotropy. 8. 25 g of hexane was slowly added to the concentrated solution with stirring to precipitate crystals, followed by continued stirring in an ice bath for 2 hours. 9. The precipitated crystals were separated by filtration and dried under vacuum to afford 15.4 g of (S)-3-tert-butoxycarbonylaminopyrrolidine in 87.4% yield, 99.5% chemical purity, 99.5% optical purity ee, and 0.4% water content.

References

[1] Tetrahedron Asymmetry, 2010, vol. 21, # 11-12, p. 1511 - 1521
[2] Patent: EP1640364, 2006, A1. Location in patent: Page/Page column 10-11

(S)-3-(Boc-amino)pyrrolidine(122536-76-9)Related Product Information

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