N-BOC-3-BROMOPYRROLIDINE Chemical Properties

Melting point:

47-52℃

Boiling point:

277.5±33.0 °C(Predicted)

Density 

1.379±0.06 g/cm3(Predicted)

Flash point:

>110°C

storage temp. 

2-8°C

pka

-3.30±0.40(Predicted)

form 

solid

Appearance

White to yellow Solid

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C9H16BrNO2/c1-9(2,3)13-8(12)11-5-4-7(10)6-11/h7H,4-6H2,1-3H3

InChIKey

QJTKPXFJOXKUEY-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCC(Br)C1

CAS DataBase Reference

939793-16-5

Safety Information

Hazard Codes 

Xn,N

Risk Statements 

22-36-50

Safety Statements 

26-61

RIDADR 

UN 3077 9/PG 3

WGK Germany 

3

HazardClass 

9

HS Code 

2933998090

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral
Aquatic Acute 1
Eye Irrit. 2

N-BOC-3-BROMOPYRROLIDINE Usage And Synthesis

Uses

(±)-1-Boc-3-bromopyrrolidine is used in organic synthesis.

Synthesis

General procedure for the synthesis of N-BOC-3-bromopyrrolidine from (RS)-1-tert-butoxycarbonyl-3-hydroxypyrrolidine: (RS)-1-tert-butoxycarbonyl-3-hydroxypyrrolidine (3.00 g) was dissolved in THF (90 mL), and triphenylphosphine (12.4 g) and carbon tetrabromide (15.7 g) were added sequentially. Subsequently, THF (90 mL) was added slowly dropwise and the reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the organic solvent was removed by rotary evaporation. The residue was extracted with ethyl acetate (4 x 50 mL), and the combined organic phases were washed with deionized water, dried over anhydrous sodium sulfate, and rotary evaporated again to dryness. Finally, the residue was purified by fast column chromatography (silica gel, cyclohexane/ethyl acetate 80/20) to afford the target product, (RS)-1-tert-butoxycarbonyl-3-bromopyrrolidine, in 80% yield as a yellow oil.1H-NMR (300 MHz, DMSO-d6, δ ppm relative to TMS): δ 4.85 (1H, m) 3.70-3.59 (1H, m), 3.55-2.10 (5H, m), 1.35 (9H, s).

References

[1] Journal of the American Chemical Society, 2016, vol. 138, # 24, p. 7520 - 7523
[2] Patent: WO2007/118830, 2007, A1. Location in patent: Page/Page column 139
[3] Patent: WO2010/51245, 2010, A1. Location in patent: Page/Page column 38
[4] Patent: WO2010/77624, 2010, A1. Location in patent: Page/Page column 37
[5] Journal of Medicinal Chemistry, 2017, vol. 60, # 13, p. 5613 - 5637

N-BOC-3-BROMOPYRROLIDINE(939793-16-5)Related Product Information

• 1-N-Boc-3-Cyanopyrrolidine
• (S)-1-BOC-3-Cyanopyrrolidine
• (R)-1-Boc-3-cyanopyrrolidine
• (R)-N-Boc-3-(aminomethyl)pyrrolidine
• (R)-1-Boc-3-(aminomethyl)pyrrolidine
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