Lithium triethylborohydride → HCID 131736455, compound

Participants

Reaction Conditions

Reaction Steps

SEM dilactam 14d (0.223 g, 0.183 mmol, 1.0 eq.) was solubilised in THF (10 mL) and cooled to −78° C. under a nitrogen atmosphere. Super hydride solution (0.373 mL, 0.373 mmol, 2.04 eq.). was added dropwise over 5 minutes. After 20 minutes an aliquot was washed with water for LCMS and TLC analysis and after 30 minutes water (30 mL) was added and the cold bath removed. The organic layer was extracted with EtOAc (2×30 mL) and the combined organic extracts washed with brine (30 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was dissolved in MeOH (12 mL), DCM (6 mL) and water (2 mL) and enough silica gel to form a thick stirring suspension which was left for 5 days. The suspension was filtered and washed with DCM/MeOH 9:1 (˜200 mL) until complete elution of product. The organic layer was washed with brine (2×70 mL), dried over MgSO4, filtered and concentrated under reduced pressure and the residue was purified by flash chromatography (silica gel, 100/0 to 90/10 v/v CHCl3/MeOH) to afford the product as a yellow solid (0.133 g, 79%). LC/MS (2.916 min (ES+)), m/z: 926.33 [M+H]+.

Provenance & Evidence