HCID 67155119, compound → HCID 67022355, compound

Participants

Reaction Conditions

Reaction Steps

To 2 (1.053 g, 4.09 mmol) in HPLC MeOH (20 mL) at −78° C. was added portion-wise KBH4 (764.3 mg, 14.2 mmol), and the resulting reaction mixture was stirred for 45 min before being warmed to −20° C., and being stirred for a further 30 min at that temperature. The mixture was then warmed to 0° C. and stirred for a further 2 h, after which the mixture was quenched with AcOH until the pH was below 7. The mixture was then concentrated in vacuo, and EtOAc (70 mL) was added followed by water (40 mL). The layers were separated and the aqueous phase was extracted with EtOAc (60 mL). The organic extracts were combined, washed with saturated brine (60 mL), dried (MgSO4) and concentrated in vacuo. Purification was performed by flash column chromatography on silica (eluant 3:7-4:6-1:1 EtOAc/Hexane) to give 3 (436 mg, 1.68 mmol, 41%) as a white solid (diastereoisomers 1:1 ratio).

Provenance & Evidence