(S)-(-)-1-tert-Butoxycarbonyl-3-aminopyrrolidine Chemical Properties

alpha 

-2 º (c=1, chloroform)

Boiling point:

216-217 °C(lit.)

Density 

1.067 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.4720(lit.)

Flash point:

196 °F

storage temp. 

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

form 

Liquid

pka

9.55±0.20(Predicted)

color 

Clear colorless to yellow

optical activity

[α]20/D 2°, c = 1 in chloroform

Sensitive 

Air Sensitive

BRN 

8312125

InChI

InChI=1S/C9H18N2O2/c1-9(2,3)13-8(12)11-5-4-7(10)6-11/h7H,4-6,10H2,1-3H3/t7-/m0/s1

InChIKey

CMIBWIAICVBURI-ZETCQYMHSA-N

SMILES

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

CAS DataBase Reference

147081-44-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,C,Xi

Risk Statements 

22-41

Safety Statements 

26

RIDADR 

UN 2810 6.1/PG 3

WGK Germany 

2

HazardClass 

8

PackingGroup 

III

HS Code 

29339900

MSDS

• Language:English Provider:(S)-(-)-1-tert-Butoxycarbonyl-3-aminopyrrolidine
• Language:English Provider:SigmaAldrich
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(S)-(-)-1-tert-Butoxycarbonyl-3-aminopyrrolidine Usage And Synthesis

Chemical Properties

Colorless to light yellow liqui

Uses

(S)-(-)-1-Boc-3-aminopyrrolidine may be used to prepare:

• Descarboxamide analog of 4-N-(N^ω-nitro-L-argininyl)-trans-4-amino-L-proline amide.
• Histamine 3 (H₃) receptor antagonists containing pyrrolidin-3-yl-N-methylbenzamide moiety.

Synthesis

To a solution of compound 178 (2.0 g, 9.42 mmol, 1.0 eq.) in methanol (40 mL) was added palladium carbon (1.0 g, 0.94 mmol, 0.1 eq.). The reaction mixture was subjected to hydrogenation at atmospheric pressure and room temperature for 6 hours. After completion of the reaction, the reaction mixture was filtered through diatomaceous earth and the filtrate was concentrated under reduced pressure. The target compound (S)-1-Boc-3-aminopyrrolidine was obtained as a yellow oil (1.7 g, 97% yield).

References

[1] Patent: US2009/221565, 2009, A1. Location in patent: Page/Page column 51
[2] Patent: WO2016/34134, 2016, A1. Location in patent: Paragraph 00470
[3] Patent: CN105399698, 2016, A. Location in patent: Paragraph 1340-1342
[4] Patent: WO2005/811, 2005, A1. Location in patent: Page/Page column 61
[5] Patent: WO2005/20975, 2005, A2. Location in patent: Page/Page column 221

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