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ChemicalBook CAS DataBase List BOC-TRANS-4-FLUORO-L-PROLINE METHYL ESTER
203866-18-6

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

11synthesis methods
-

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

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