ChemicalBook CAS DataBase List BOC-TRANS-4-FLUORO-L-PROLINE METHYL ESTER

BOC-TRANS-4-FLUORO-L-PROLINE METHYL ESTER synthesis

11synthesis methods

Product Name:BOC-TRANS-4-FLUORO-L-PROLINE METHYL ESTER
CAS Number:203866-18-6
Molecular formula:C11H18FNO4
Molecular Weight:247.26

1-(1,1-Dimethylethyl) (2S,4R)-4-fluoro-1,2-pyrrolidinedicarboxylate

203866-14-2

74-88-4

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

203866-18-6

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.

203866-14-2 Synthesis

203866-14-2
229 suppliers
$23.30/1G

74-88-4
349 suppliers
$15.00/10g

203866-18-6
143 suppliers
$14.00/250mg

Yield:203866-18-6 95.3%

Reaction Conditions:

with potassium carbonate in N,N-dimethyl-formamide at 0 - 20; for 2 h;Inert atmosphere;

Steps:

1.1 Step 1: (2S,4R)-1-tert-Butyl 2-methyl 4-fluoropyrrolidine-1,2-dicarboxylate (37-2):

To a solution of compound 37-1 (1.0 g, 4.29 mmol) in DMF (10mL) was added K₂CO₃ (1.18 g, 8.58 mmol) followed by MeI (1.83 g,12.9 mmol) at 0 °C and the mixture was stirred at room temperature under N2 atmosphere for 2 hours. The mixture was poured into iced-water and extracted with EtOAc twice. The combined organic layers were washed with saturated aqueous NH₄Cl solution and brine, dried with anhydrous Na₂SO₄, filtered and concentrated to dryness. The residue was purified by chromatography on silica gel (eluted with PE: EtOAc= 20: 1) to afford compound 37-2 (1.01 g, yield 95.3%) as a light yellow oil. LC/MS (ESI)m/z: 248 (M+H)⁺.

References:

WO2020/41301,2020,A1 Location in patent:Page/Page column 289; 338-339

74844-91-0 Synthesis