HCID 89471697, compound → HCID 178483375, compound

Participants

Reaction Conditions

Reaction Steps

Compound 2 (0.041 g, 0.04 mmol) was dissolved in anhydrous THF (3.8 mL) under an argon atmosphere and cooled to −78° C. in an acetone-dry ice bath. LiEt3BH (0.25 mL of a 1M solution in THF, 0.35 mmol, 6 eq) was added to the mixture, and the reaction was stirred at −78° C. for 40 minutes. The reaction was quenched with H2O (3 mL) and after addition of brine (3 mL) the aqueous phase was extracted (DCM, 9 mL-methanol 1 mL), dried (MgSO4) and the solvent was removed by rotary evaporation under reduced pressure. The crude was dissolved in a mixture of ethanol (3 mL), DCM (1.5 mL) and H2O (1.5 mL) and silica gel was added to the mixture. The reaction was stirred for four days at room temperature under an atmosphere of Argon. The mixture was filtered over a sinter funnel washing with a mixture of DMC (140 mL) and methanol (15 mL). The organic phase was washed with brine (200 mL), dried (MgSO4) and the solvent was removed by rotary evaporation under reduced pressure. The resulting brown solid was purified by flash column chromatography (silica gel, gradient 90% DCM-10% methanol). Compound 3 was obtained as a brown solid (0.029 g, 59%); Rf 0.11 [8% methanol in DCM]; LC-MS (5 min) 2.47 min, ES+ 702.28.

Provenance & Evidence