Sodium Thiosulfate → HCID 57774373, compound

Participants

Reaction Steps

tert-Butyl 4-(2-(hydroxymethyl)phenyl)piperidine-1-carboxylate (216 mg, 0.74 mmol, 1 eq.) and Dess Martin periodinane (377 mg, 1.2 eq., 0.89 mmol) were stirred in DCM (7 mL) for 1 h. HPLC and LCMS showed completion of the reaction. Sodium thiosulfate was then added and the biphasic mixture was stirred for 10 min, then the mixture was diluted with EtOAc (50 mL), the biphasic mixture was separated, the organics were dried (MgSO4), conc in vacuo and purified by ISCO chromatography (8 g SiO2, 0 to 15% EtOAc in Hexanes). Remaining DMP side product was observed so the residue was taken up in DCM, the insolubles filtered off, the filtrate concentrated and purified by ISCO chromatography (12 g SiO2, 0 to 10% EtOAc in Hexanes) to give, after concentration, 229 mg of tert-butyl 4-(2-formylphenyl)piperidine-1-carboxylate as a clear oil (still contains some DMP side product) which was used in the next step without further purification. LC/MS ES+1-Boc: 190.08.

Provenance & Evidence