Water → HCID 54257403, compound

Participants

Reaction Conditions

Reaction Steps

The product from Step D (430 mg, 0.91 mmol) was taken up in acetonitrile (1.5 mL) with stirring and cooled to 0° C. RuCl3.3H2O (0.5 mg) and NalO4 (290 mg, 1.37 mmol) were added followed by water (2 mL). The resulting mixture was stirred at room temperature for 2½h until tlc (hex/EtOAc 1:1) indicated the absence of starting material. The reaction was diluted with DCM, the layers separated and the aqueous layer was further extracted with DCM. The organic extracts were combined, dried, filtered and concentrated in vacuo to give the product as an oil (360 mg, 81%). 1H-NMR δ (CDCl3) 7.37-7.09 (15H, m), 4.96 (1H, d, J=12.2 Hz), 4.94 (1H, d, J=12.1 Hz), 3.91 (1H, m), 3.89-3.68 (2H, m), 3.31 (1H, dd, J=4.5, 14.0 Hz), 2.88-2.45 (7H, m 1.72-1.50 (3H, m) and 1.29-1.15 (2H, m).

Provenance & Evidence