BOC-TRANS-4-FLUORO-L-PROLINE METHYL ESTER Chemical Properties

Melting point:

34-39 °C

Density 

1.16

Flash point:

110 °C

storage temp. 

2-8°C

form 

powder

Appearance

Colorless to off-white <36°C Solid,>39°C Liquid

optical activity

[α]22/D -80.0°, c = 1 in methanol

Water Solubility 

Insoluble in water.

InChI

InChI=1S/C11H18FNO4/c1-11(2,3)17-10(15)13-6-7(12)5-8(13)9(14)16-4/h7-8H,5-6H2,1-4H3/t7-,8+/m1/s1

InChIKey

METPQQHVRNLTRX-SFYZADRCSA-N

SMILES

N1(C(OC(C)(C)C)=O)C[C@H](F)C[C@H]1C(OC)=O

Safety Information

WGK Germany 

3

HS Code 

2933998090

BOC-TRANS-4-FLUORO-L-PROLINE METHYL ESTER Usage And Synthesis

Uses

N-Boc-trans-4-fluoro-L-proline methyl ester is used to prepare (S)-2-[N-(N'-benzyl-(S)-4-fluoro-L-prolyl)amino]benzophenone by reacting with of 2-aminobenzophenone in the presence of potassium tert -butoxide.

Synthesis

GENERAL STEPS: (2S,4R)-1-[(tert-butoxy)carbonyl]-4-fluoropyrrolidine-2-carboxylic acid (2 g, 8.57 mmol), potassium carbonate (5.9 g, 42.69 mmol), and THF (80 mL) were mixed, and methyl iodide (6.1 g, 42.98 mmol) was added, and the reaction was stirred for 12 hours at room temperature. After completion of the reaction, the solid was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by rapid chromatography on silica gel with EtOAc/petroleum ether (1:5) as eluent to afford N-BOC-trans-4-fluoro-L-proline methyl ester (800 mg, 38% yield) as a colorless oil.

References

[1] Patent: WO2015/52264, 2015, A1. Location in patent: Paragraph 0521; 0522; 01714; 01715

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