Potassium bis(trimethylsilyl)amide → 7-Methylene-5-(1-phenyl-ethyl)-3b,4,5,6,6a,7-hexahydro-1-thia-5-aza-cyclopenta[alpha]pentalene

Participants

Reaction Conditions

Reaction Steps

Potassium bis(trimethylsilyl)amide (308 mg, 1.55 mmol) was added to a solution of methyl triphenylphosphonium bromide (575 mg, 1.61 mmol) in 7 mL of THF at 0° C. After 30 minutes of stirring at 0° C., the product from step e) (303 mg, 1.07 mmol) dissolved in 2 mL of THF was added to the reaction mixture and was allowed to come to room temperature over 1 hour. The reaction mixture was diluted with dichloromethane (30 mL) and was washed with brine, dried (MgSO4) and concentrated to an oil. The crude was purified by column chromatography (SiO2) using 5-55% ethylacetate-hexane gradient to afford the subtitle compound (226 mg, yield: 74.8%). MS calculated for C18H19NS +H: 282, observed: 282.

Provenance & Evidence