(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid → HCID 58005112, compound

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Reaction Steps

To a 0.2 mM solution of trans 4-hydroxy L-BOC-proline (1 eq) in DMSO at RT was added tBuOK (3 eq) in a single portion. The reaction mixture was stirred at RT for 30 min, cooled to 10° C. and 7-bromo-1-chloroisoquinoline was added (1 eq). The resulting mixture was allowed to warm to RT and stirred overnight. The organic layer was washed with sat. aq. citric acid solution, water and brine and the aqueous phases were back extracted with EtOAc. The combined organic phases were dried (Na2SO4) and the solvent evaporated under reduced pressure to give a dark solid. The solid was dissolved in MeOH and to the stirred solution an excess (4 eq) of 2.0 M trimethylsilyldiazomethane in hexanes was added dropwise at 15° C. The resulting mixture was stirred for 15 min after gas evolution has ceased. Volatiles were removed by rotary evaporation and the residue was purified by flash chromatography (SiO2, PE/EtOAc 8/2 v/v as eluent) to give title product as a solid. MS (ES+) C20H23BrN2O5 requires 451. Found: 452 (M+H+).

Provenance & Evidence