Hydrochloric Acid → HCID 10388783, compound

Participants

Reaction Conditions

Reaction Steps

Title compound of example 9 (0.5 g, 1.1 mmol) was dissolved in 5 ml DCM and was then slowly added at −70° C. to a mixture of 0.29 ml (2.8 mmol) oxalyl chloride, 0.39 ml (5.6 mmol) dimethyl sulfoxide and in 13 ml DCM. Stirring was continued at −70° C. for 3 hours, then the mixture was allowed to warm up to −50° C. and 1.5 ml (11.0 mmol) NEt3 and 20 ml water were added and the mixture was extracted with DCM. The organic layer was evaporated and immediately used for next step. The crude aldehyde was dissolved in 8 ml MeOH and 1.0 g (13.5 mmol) ammonium acetate and 62.8 mg (0.95 mmol) sodium cyanoborohydride were added. This mixture was stirred at room temperature over night, then 2 ml 1N HCl were added and stirring continued for 30 min. 2N NaOH was added to reach basic pH, and the mixture was extracted with DCM. The title compound was purified by chromatography (SiO2, ethyl acetate/MeOH/NH3conc. 90/10/1) and was isolated as a pale solid (25 mg, 5%)

Provenance & Evidence