Sodium Thiosulfate → HCID 90200952, compound

Participants

Reaction Steps

Rac-(7aR,11aS)-11a-(Pyridin-2-ylmethyl)-5,6,7,7a,8,10,11,11a-octahydro spiro[benzo[6,7]cyclohepta[1,2-c]pyridine-9,2′-[1,3]dioxolane]-3-carbaldehyde (146, R2=Pyridin-2-ylmethyl) (0.400 g, 1.06 mmol) and THF (10 mL) were added to a round bottom flask and stirred. (4-Fluorophenyl)magnesium bromide (2M in diethyl ether) (0.95 mL, 1.90 mmol) was added and the mixture was stirred at rt for about 1 h. Sat. aq. NH4Cl was added and the product was extracted with EtOAc (15 mL), dried over MgSO4 and concentrated in vacuo. The residue was taken into DCM (6 mL) and stirred at rt. Dess-Martin periodinane (0.556 g, 1.31 mmol) was added and mixture was stirred at rt for about 2 h. Sat. aq. NaHCO3 (5 mL) and sat. aq. Na2S2O3 (5 mL) were added and the resulting mixture was extracted with EtOAc (15 mL), dried over Na2SO4 and concentrated in vacuo.

Provenance & Evidence